DOCSLIB.ORG

M.Sc (ORGANIC CHEMISTRY) LABORATORY MANUAL

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
M.Sc (ORGANIC CHEMISTRY) LABORATORY MANUAL M.Sc (ORGANIC CHEMISTRY) LABORATORY MANUAL DEPARTMENT OF CHEMISTRY RAJA BAHADUR VENKATA RAMA REDDY WOMEN’S COLLEGE (Autonomous) Affiliated to Osmania University Accredited by NAAC with ‘A’ Grade College with Potential for Excellence (Selected by UGC) Narayanaguda, Hyderabad, Telangana State SYNTHESIS OF ORGANIC COMPOUNDS INDEX S. No Contents Page No. 1. Synthesis of Organic Compounds 1-31 2. Multi step synthesis of Organic Compounds 35-77 3. Isolation of Natural Products 79-85 4. Synthesis of Drugs 87-107 5. Separation of Organic binary & ternary mixtures 109-115 6. Qualitative Analysis of Organic Compounds 117-135 7. Spectral Analysis of Unknown Organic compounds 137-145 8. Chromatography 147-166 9. Estimation of Drugs 167-201 10. Microwave Assisted Organic Synthesis 202 CONTENTS 1. ACETANILIDE 2. P-BROMO ACETANILIDE 3. P-BROMO ANILINE 4. 2,4,6-TRIBROMO ANILINE 5. ASPIRIN 6. HIPPURIC ACID 7. TETRA-HYDRO CARBAZOLE 8. PHTHALIMIDE 9. META-DINITRO BENZENE 10. META NITRO ANILINE 11. ANTHRACENE-MALEIC ANHYDRIDE ADDUCT 12. 2,4- DIHYDROXY ACETOPHENONE 13. 7-HYDROXY-4-METHYL COUMARIN 14. AZALACTONE Department of Chemistry, RBVRRWC 1 2017-2018 ACETANILIDE General Reaction O NH2 NH C CH3 O O CH3COOH CH COOH O 3 Aniline Acetic Anhydride Acetanilide Mechanism O O O O C C NH2 H2N CH CH O O 3 3 O O H O C NH C CH3 H3C N H C O CH3 CH3COOH Acetanilide Department of Chemistry, RBVRRWC 2 2017-2018 PREPARATION OF ACETANILIDE Aim: To study N-acylation. Principle: Aniline undergoes N-acylation with acetic anhydride in the presence of glacial acetic acid, preferentially attacking the nitrogen atom of aniline. Reaction:N-acylation / N-acetylation / Electrophilic Substitution Reaction. Chemicals: Aniline - 5mL Glacial acetic acid - 5mL Acetic anhydride - 5mL Apparatus: R. B. Flask, Beaker, Water condenser. Procedure: Transfer 5mLof Aniline into a clean & dry round bottomed flask, add 5mL of glacial acetic acid and 5mL of acetic anhydride. Add a porcelain piece and fix the water condenser and boil the mixture for 15 minutes on bunsen flame. Test for the completion of reaction by transferring a few drops of mixture into a beaker containing 100mL of cold water. If white precipitate is formed, it indicates that the reaction is completed. If no precipitate is formed continue heating for 10 more minutes and check for completion of the reaction.Then transfer the reaction mixture into beaker containing cold water & stir with a glass rod. Filter the compound under suction. Wash the precipitate with cold water & dry the sample. Recrystallisation: Solvent-Hot water M.P: 1140C Department of Chemistry, RBVRRWC 3 2017-2018 Department of Chemistry, RBVRRWC 4 2017-2018 PREPARATION OF P-BROMO ACETANILIDE Aim: To study the orientation of Electrophilic Substitution Reaction. Principle: Aniline undergoes electrophilic substitution with bromine at 2, 4, 6 – positions to form tribromo aniline. To substitute selectively, the amino group has to be protected by acylation such that the bulky group restricts electrophilic substitution at ortho position because of steric hindrance & directs to para position. Reaction : Electrophilic Substitution Reaction. Chemicals: Acetanilide – 4gms Glacial CH3COOH – 10mL Bromine in glacial CH3COOH – 10mL Apparatus: Conical flask, beaker &glass rod Procedure: Dissolve 4gms of finely powdered acetanilide in 10mL of cold glacial acetic acid in a 250mL conical flask. In another small flask take 10mL of bromine in acetic acid and add this solution slowly into acetanilide solution until reddish orange colour persists. Shake the reaction mixture throughout the addition to ensure thorough mixing. Allow the final mixture to stand at room temperature for 15 minutes with occasional stirring. Then pour the reddish orange solution which may already contain some crystals of p-bromo acetanilide into a large amount of cold water, where upon p-bromo acetanilide will readily crystallizes out. Stir these crystals thoroughly with water to eliminate CH3COOH & wash it with cold water & filter. Recrystallisation: Solvent-Rectified Spirit M.P: 163oC Department of Chemistry, RBVRRWC 5 2017-2018 Department of Chemistry, RBVRRWC 6 2017-2018 PREPARATION OF P-BROMO ANILINE Aim: To study hydrolysis of p-bromo acetanilide Principle: p-bromo acetanilide undergoes hydrolysis in the presence of conc.HCl to form p-bromo aniline. Reaction: Hydrolysis (deacylation) Chemicals: Para bromo acetanilide – 4gms Conc HCl-5mL Ethyl alcohol – 8mL 5% NaOH Apparatus: R.B. flask, water condenser Procedure: Dissolve 4g of p-bromo acetanilide in 8mL of boiling ethanol contained in a 100mL round bottomed flask. Add 5mL of conc. HCl drop wise to the boiling solution. Reflux for 30-40 minutes. Dilute the reaction mixture with 50mL of water where by p-bromo aniline is formed. Neutralize the acidic solution with 5% NaOH until alkaline. Para bromo aniline separates as oil, which crystallizes by adding ice and filter. Recrystallisation: Solvent-Alcohol M.P: 66oC Department of Chemistry, RBVRRWC 7 2017-2018 2,4,62,4,6 -T TRIBROMORIBROMO A NANILINEILINE General reaction NH NH2 2 Br Br CH3COOH 3 Br2 Mechanism Br Formation of Electrophile O O H3C C OH H3C C O H Br Br H H Br Br Electrophile Formation of Sigma Complex NH2 NH2 NH2 NH2 NH2 Resonance hybrid Attack of Electrophile NH 2 NH2 NH2 NH2 Br H Br H Br Br Br NH2 NH NH 2 NH2 2 Br H Br Br Br Br Br Br Br NH2 Br NH2 NH2 Br H Br Br Br Br Br Br Br 2,4,6-TRIBROMO ANILINE 2,4,6 Tribromo aniline Department of Chemistry, RBVRRWC 8 2017-2018 PREPARATION OF 2, 4, 6–TRIBROMO ANILINE Aim: To study Electrophilic Substitution Reaction (bromination) on aniline Principle: Aniline readily undergoes Electrophilic Substitution Reaction by involving the non-bonding electrons present on nitrogen. As NH2group is Ortho& Para directing and also ring activating group there is an increase in electron density at ortho and para positions. Therefore aniline on bromination gives 2,4,6- tribromo aniline (i.e) bromination takes place at 2,4&6 positions. Reaction:Electrophilic Substitution Reaction (Bromination) Chemicals: Aniline – 5mL Acetic acid – 19mL Bromine in CH3COOH – 30mL. Apparatus: Beaker, Funnel, Measuring jar, Glass rod. Procedure: Take 5mL of aniline and 19mL ofglacial acetic acid in conical flask & keep this flask in ice bath and then add 30mL of Br2in acetic acid drop wise with constant stirring till orange colour of bromine persists. Allow the solution to stand at room temp for 15 minutes. Pour it into the cold water. 2,4,6-tribromo aniline precipitates out and filter. Recrystallisation: Solvent- Ethyl Alcohol M.P: 1200C Department of Chemistry, RBVRRWC 9 2017-2018 ASPIRIN General Reaction O OH O C CH COOH 3 O O COOH Conc. H2SO4 CH3COOH O Salicylic Acid Acetic Anhydride Aspirin Mechanism H O O O O H O O H O O H O O O H O OH HO O O HOOC HOOC HOOC CH3COOH - H O O C CH3 COOH Aspirin Department of Chemistry, RBVRRWC 10 2017-2018 PREPARATION OF ASPIRIN Aim: To prepare aspirin by O-acylation Principle: Salicylic acid undergoes acetylation with acetic anhydride selectively at the weakly acidic group (i.e.) phenolic group into strongly acidic group in the presence of conc. H2SO4as catalyst. Reaction: Electrophilic Substitution Reaction /O-Acetylation / O-Acylation Chemicals: Salicylic acid – 2gms Acetic anhydride– 2.8mL Conc.H2SO4- 2-3 drops Apparatus: Conical flask, glass rod. Procedure: Weigh about 2gms of salicylic acid and transfer into a clean conical flask and add 2.8mL of acetic anhydride and stir it with a glass rod and add 2-3 drops of conc. H2SO4 and stir the mixture and warm on water bath to about 50-60oC for 15 minutes. Allow the mixture to cool and add about 50mL of water. Stir well and filter at the pump. Recrystallisation: Solvent-Equal amounts of acetic acid and water M.P:1360C Department of Chemistry, RBVRRWC 11 2017-2018 -HCl HIPPURIC ACID Genearal reaction O O O Cl NaOH H2N H OH N O Benzoyl Chloride H Glycine Hippuric Acid O Mechanism O NaOOC CH2 O O O NaOH Ph Cl HN C Ph H2N NH2 OH H2O NaO H Cl -HCl CH2COONa O O HOH H HN C N NaOH HO O Hippuric Acid Department of Chemistry, RBVRRWC 12 2017-2018 PREPARATION OF HIPPURIC ACID Aim: To study N-Benzoylation Principle: Electrophilic substitution of benzoyl group on nitrogen atom of glycine gives N-Benzoyl glycine, commonly known as Hippuric acid. Reaction: N-Benzoylation of glycine. Chemicals: Glycine - 2.5gm 10% NaOH – 2.5mL Benzoyl chloride – 4.5mL Apparatus: Conical flask, glass rod,cork Procedure: Dissolve 2.5 gms of glycine in 2.5mL of 10% NaOH solution taken in a conical flask (if not dissolved add few more mL of 10% NaOH) and add 4.5mL of benzoyl chloride in two portions to the solution. Stopper the flask and shake vigorously after each addition. Transfer the solution into a beaker containing water & filter it. If product is not formed, add crushed ice. Recrystallisation: Solvent – Boiling water M.P: 1870C Department of Chemistry, RBVRRWC 13 2017-2018 TETRA HYDRO CARBAZOLE General Reaction AcOH NH NH2 O N H Phenyl Hydrazene Cyclohexanone Tetra Hydro Carbazole Mechanism Ph Ph H NH N Ph NH NH2 HN N O H H O HO -H2O H H H N N HN N H H Ph H H H NH3 NH HN N H H2N N H Tetra Hydro Carbazole Department of Chemistry, RBVRRWC 14 2017-2018 PREPARATION OF TETRA – HYDRO CARBAZOLE Aim: To study Fischer Indole synthesis. Principle: Fischer Indolization occurs when phenyl hydrazine reacts with saturated cyclic aldehyde or ketone. Cyclization takes place with loss of NH3 under the influence of reagents like glacial acetic acid. Phenyl hydrazine of saturated cyclic ketone like cyclohexanone undergoes cyclisation very rapidly when boiled with glacial acetic acid.
Load more

Recommended publications
  • Retention Indices for Frequently Reported Compounds of Plant Essential Oils
    Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5.
    [Show full text]
  • Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances 2017
    INTERNATIONAL NARCOTICS CONTROL BOARD Precursors and chemicals frequently used in the illicit manufacture of narcotic drugs and psychotropic substances 2017 EMBARGO Observe release date: Not to be published or broadcast before Thursday, 1 March 2018, at 1100 hours (CET) UNITED NATIONS CAUTION Reports published by the International Narcotics Control Board in 2017 The Report of the International Narcotics Control Board for 2017 (E/INCB/2017/1) is supplemented by the following reports: Narcotic Drugs: Estimated World Requirements for 2018—Statistics for 2016 (E/INCB/2017/2) Psychotropic Substances: Statistics for 2016—Assessments of Annual Medical and Scientific Requirements for Substances in Schedules II, III and IV of the Convention on Psychotropic Substances of 1971 (E/INCB/2017/3) Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances: Report of the International Narcotics Control Board for 2017 on the Implementation of Article 12 of the United Nations Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances of 1988 (E/INCB/2017/4) The updated lists of substances under international control, comprising narcotic drugs, psychotropic substances and substances frequently used in the illicit manufacture of narcotic drugs and psychotropic substances, are contained in the latest editions of the annexes to the statistical forms (“Yellow List”, “Green List” and “Red List”), which are also issued by the Board. Contacting the International Narcotics Control Board The secretariat of the Board may be reached at the following address: Vienna International Centre Room E-1339 P.O. Box 500 1400 Vienna Austria In addition, the following may be used to contact the secretariat: Telephone: (+43-1) 26060 Fax: (+43-1) 26060-5867 or 26060-5868 Email: [email protected] The text of the present report is also available on the website of the Board (www.incb.org).
    [Show full text]
  • Application of Biomarker Compounds As Tracers for Sources and Fates of Natural and Anthropogenic Organic Matter in Tile Environment
    AN ABSTRACT OF THE DISSERTATION OF Daniel R. Oros for the degree of Doctor of Philosophy in Environmental Sciences presented on September 24. 1999. Title: Application of Biomarker Compoundsas Tracers for Sources and Fates of Natural and Anthropogenic Organic Matter in the Environment. Redacted for Privacy Abstract approved: Bernd R.T. Simoneit Determination of the source and fate of natural (higher plant lipids, marine lipids, etc.) and anthropogenically (e.g., petroleum, coal emissions) derived hydrocarbons and oxygenated compounds in the environment was accomplished using gas chromatography (GC) and gas chromatography-mass spectrometry (GC- MS) to characterize or identify molecular biomarkers to be utilized as tracers. The distributions and abundances of biomarkers such as straight chain homologous series (e.g., n-alkanes, n-alkanoic acids, n-alkan-2-ones, n-alkanols, etc.) and cyclic terpenoid compounds (e.g., sesquiterpenoids, diterpenoids, steroids, triterpenoids) were identified in epicuticular waxes from conifers of western North America (natural emissions). These biomarkers and their thermal alteration derivativeswere also identified in smoke emissions from known vegetation sources (e.g., conifers, deciduous trees and grasses) and were then applied as tracers in soils, soils that contained wildfire residues and soillriver mud washout after wildfire burning. Where possible, the reaction pathways of transformation from the parentprecursor compounds to intermediate and final alteration products were determined from GC- MS data. In addition, molecular tracer analysis was applied to air, water and sediment samples collected from a lacustrine setting (Crater Lake, OR) in order to determine the identities, levels and fates of anthropogenic (i.e., petroleum hydrocarbon contamination from boating and related activities) hydrocarbons ina pristine organic matter sink.
    [Show full text]
  • Metabolomics Analysis Reveals Large Effects of Gut Microflora on Mammalian Blood Metabolites
    Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites William R. Wikoffa, Andrew T. Anforab, Jun Liub, Peter G. Schultzb,1, Scott A. Lesleyb, Eric C. Petersb, and Gary Siuzdaka,1 aDepartment of Molecular Biology and Center for Mass Spectrometry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037; and bGenomics Institute of the Novartis Research Foundation, San Diego, CA 92121 Communicated by Steve A. Kay, University of California at San Diego, La Jolla, CA, December 19, 2008 (received for review December 12, 2008) Although it has long been recognized that the enteric community of found to extract energy from their food more efficiently compared bacteria that inhabit the human distal intestinal track broadly impacts with lean counterparts due to alterations in the composition of their human health, the biochemical details that underlie these effects gut microflora that resulted in an increased complement of genes remain largely undefined. Here, we report a broad MS-based metabo- for polysaccharide metabolism (10). It has also been observed that lomics study that demonstrates a surprisingly large effect of the gut bile salt hydrolase encoding genes are enriched in the gut micro- ‘‘microbiome’’ on mammalian blood metabolites. Plasma extracts biome, and that enteric bacteria carry out a wide range of bile acid from germ-free mice were compared with samples from conventional modifications (6, 14). These metagenomic studies suggest that the (conv) animals by using various MS-based methods. Hundreds of metabolites derived from this diverse microbial community can features were detected in only 1 sample set, with the majority of have a direct role in human health and disease.
    [Show full text]
  • Technical Data Sheet Polyproof Phenol Resorcinol Adhesive with Hardener
    a TECHNICAL DATA SHEET POLYPROOF PHENOL RESORCINOL ADHESIVE WITH HARDENER The combination Polyproof Adhesive with hardener is approved by NTI, Norway, Otto-Graf Institut (FMPA), Germany, SKH/KOMO (DHBC No. 32389), Holland for the production of load-bearing timber structures. Polyproof can be used in door production, lamination, finger jointing and other applications in the wood working industry, where there is demand for high water and weather resistance of the joints. The combination has short pressing times even at lower pressing temperatures. PRODUCT DESCRIPTION This super-professional, two part glue has been specially developed for waterproof exterior use and can stand continuous immersion in water. This glue is so waterproof - boat builders use it. Developed for the marine industry this is the only completely waterproof adhesive that will withstand continual immersion in water. For use externally where extreme weathering will take place. Arches for bridge work, concrete formers, marine craft construction, bonding of preservative treated timber.. Bonding of difficult timber i.e. teak and Iroko. Fire resistant to class 0. Used extensively for bonding difficult timbers such as teak and iroko where normal adhesives could fail.• structural timber • laminated roof members • timber in constant contact with water • timber in contact with the ground. DIRECTIONS FOR USE General Application for jointing To obtain the very best results the moisture content should be in the 12-14% range. Timber bought as kiln dried and stored under cover will present no problem. Perhaps as important as the glue is the preparation the joining surfaces, especially for Oak and oily timbers, Teak, Iroko etc.
    [Show full text]
  • APPENDIX G Acid Dissociation Constants
    harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPENDIX G Acid Dissociation Constants §␮ ϭ 0.1 M 0 ؍ (Ionic strength (␮ † ‡ † Name Structure* pKa Ka pKa ϫ Ϫ5 Acetic acid CH3CO2H 4.756 1.75 10 4.56 (ethanoic acid) N ϩ H3 ϫ Ϫ3 Alanine CHCH3 2.344 (CO2H) 4.53 10 2.33 ϫ Ϫ10 9.868 (NH3) 1.36 10 9.71 CO2H ϩ Ϫ5 Aminobenzene NH3 4.601 2.51 ϫ 10 4.64 (aniline) ϪO SNϩ Ϫ4 4-Aminobenzenesulfonic acid 3 H3 3.232 5.86 ϫ 10 3.01 (sulfanilic acid) ϩ NH3 ϫ Ϫ3 2-Aminobenzoic acid 2.08 (CO2H) 8.3 10 2.01 ϫ Ϫ5 (anthranilic acid) 4.96 (NH3) 1.10 10 4.78 CO2H ϩ 2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH) (2-mercaptoethylamine) —— 10.73 (NH3) ϩ ϫ Ϫ10 2-Aminoethanol HOCH2CH2NH3 9.498 3.18 10 9.52 (ethanolamine) O H ϫ Ϫ5 4.70 (NH3) (20°) 2.0 10 4.74 2-Aminophenol Ϫ 9.97 (OH) (20°) 1.05 ϫ 10 10 9.87 ϩ NH3 ϩ ϫ Ϫ10 Ammonia NH4 9.245 5.69 10 9.26 N ϩ H3 N ϩ H2 ϫ Ϫ2 1.823 (CO2H) 1.50 10 2.03 CHCH CH CH NHC ϫ Ϫ9 Arginine 2 2 2 8.991 (NH3) 1.02 10 9.00 NH —— (NH2) —— (12.1) CO2H 2 O Ϫ 2.24 5.8 ϫ 10 3 2.15 Ϫ Arsenic acid HO As OH 6.96 1.10 ϫ 10 7 6.65 Ϫ (hydrogen arsenate) (11.50) 3.2 ϫ 10 12 (11.18) OH ϫ Ϫ10 Arsenious acid As(OH)3 9.29 5.1 10 9.14 (hydrogen arsenite) N ϩ O H3 Asparagine CHCH2CNH2 —— —— 2.16 (CO2H) —— —— 8.73 (NH3) CO2H *Each acid is written in its protonated form.
    [Show full text]
  • Phenol Resorcinol Formaldehyde Resin Validation Date : 01/19/2015 Print Date : 07/08/2015 Manufacturer/Supplier/Impor : Hexion Canada, Inc
    Page:1/14 Material Safety Data Sheet FOR INDUSTRIAL USE ONLY Cascophen(TM) LT-5210Q 1. Product and company identification Product name : Cascophen(TM) LT-5210Q MSDS Number : 000000104568 Material uses : Wood Adhesives, Composites, Laminates or Related Board Products Product type : Phenol Resorcinol Formaldehyde Resin Validation date : 01/19/2015 Print date : 07/08/2015 Manufacturer/Supplier/Impor : Hexion Canada, Inc. ter 180 East Broad Street Columbus, Ohio 43215 USA Contact person : [email protected] Telephone : For additional health and safety or regulatory information, call 1 888 443 9466. Emergency telephone number : For Emergency Medical Assistance Call Health & Safety Information Services 1-866-303-6949 For Emergency Transportation Information CHEMTREC US Domestic (800) 424-9300 CHEMTREC International (703) 527-3887 CANUTEC CA Domestic (613) 996-6666 Part of the CASCO® Brand of Adhesives and Resins from Hexion Inc. 2. Hazards identification –Emergency overview Physical state : Liquid Color : Clear, reddish-brown Odor : Slight alcoholic Signal word : WARNING! Hazard statements : COMBUSTIBLE LIQUID AND VAPOR. MAY FORM EXPLOSIVE MIXTURES WITH AIR. INHALATION CAUSES HEADACHES, DIZZINESS, DROWSINESS AND NAUSEA AND MAY LEAD TO UNCONSCIOUSNESS. CAUSES EYE IRRITATION. MAY CAUSE RESPIRATORY TRACT AND SKIN IRRITATION. CONTAINS MATERIAL THAT CAN CAUSE TARGET ORGAN DAMAGE. CANCER HAZARD - CONTAINS MATERIAL WHICH CAN CAUSE Version: 9.1 Date of issue/Date of revision: 01/19/2015 Date of previous issue: 12/28/2011 Cascophen(TM) LT-5210Q Page:2/14 CANCER. Precautionary measures : Do not handle until all safety precautions have been read and understood. Obtain special instructions before use. Do not breathe vapor or mist. Use only with adequate ventilation.
    [Show full text]
  • Metabolism of [IC ]Methamphetamine in Man, the Guinea Pig and the Rat
    Biochem. J. (1972) 129, 11-22 11 Printed in Great Britain Metabolism of [IC ]Methamphetamine in Man, the Guinea Pig and the Rat By J. CALDWELL, L. G. DRING and R. T. WILLIAMS Department of Biochemistry, St. Mary's Hospital Medical School, London W.2, U.K. (Received 2 March 1972) 1. The metabolites of (±)-2-methylamino-1-phenyl[1-14C]propane ([14C]methamphet- amine) in urine were examined in man, rat and guinea pig. 2. In two male human subjects receiving the drug orally (20mg per person) about 90% ofthe 14C was excreted in the urine in 4 days. The urine ofthe first day was examined for metabolites, and the main metabolites were the unchanged drug (22% of the dose) and 4-hydroxymethamphetamine (15 %). Minor metabolites were hippuric acid, norephedrine, 4-hydroxyamphetamine, 4-hydroxy- norephedrine and an acid-labile precursor of benzyl methyl ketone. 3. In the rat some 82 % of the dose of '4C (45mg/kg) was excreted in the urine and 2-3 % in the faeces in 3-4 days. In 2 days the main metabolites in the urine were 4-hydroxymethamphetamine (31 % ofdose), 4-hydroxynorephedrine (16 %) and unchanged drug (11 %). Minor metabo- lites were amphetamine, 4-hydroxyamphetamine and benzoic acid. 4. The guinea pig was injected intraperitoneally with the drug at two doses, 10 and 45mg/kg. In both cases nearly 90% of the 14C was excreted, mainly in the urine after the lower dose, but in the urine (69%) and faeces (18%) after the higher dose. The main metabolites in the guinea pig were benzoic acid and its conjugates.
    [Show full text]
  • Chemical Science
    Chemical Science View Article Online EDGE ARTICLE View Journal | View Issue Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro- Cite this: Chem. Sci.,2017,8,7152 4H-pyrazol-4-ones† Kostiantyn O. Marichev, Estevan C. Garcia, Kartick C. Bhowmick, Daniel J. Wherritt, Hadi Arman and Michael P. Doyle * 5-Acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones, accessible from arylpropargyl phenyldiazoacetates, are highly selective acyl transfer reagents for di- and polyamines, as well as aminoalcohols and aminothiols. As reagents with a carbon-based leaving group, they have been applied for benzoyl transfer with a broad selection of substrates containing aliphatic amino in combination with other competing nucleophilic Received 20th July 2017 functional groups. The substrate scope and levels of selectivity for direct benzoyl transfer exceed those Accepted 29th August 2017 of known benzoylating reagents. With exceptional selectivity for acylation between primary amines DOI: 10.1039/c7sc03184j bound to primary and secondary carbons, these new reagents have been used in direct site-selective Creative Commons Attribution 3.0 Unported Licence. rsc.li/chemical-science monobenzoylation of aminoglycoside antibiotics. Introduction 1-position of 1,2-diaminopropane,14d selective acylation of primary amines whose carbon attachment is primary, The formation of an amide bond by acyl transfer is a classic secondary or tertiary, has received scant attention.15 chemical reaction1 that has been extensively studied2 and widely We have recently prepared a novel heterocyclic compound that applied.3 Over the years numerous acyl transfer agents have been appeared to have the potential of being a selective benzoyl transfer investigated; their activities have been dependent on the leaving reagent.
    [Show full text]
  • Preparative Method of Novel Phthalocyanines from 3- Nitro
    Available online a t www.derpharmachemica.com Scholars Research Library Der Pharma Chemica, 2012, 4(4):1397-1403 (http://derpharmachemica.com/archive.html) ISSN 0975-413X CODEN (USA): PCHHAX Preparative Method of Novel Phthalocyanines from 3- Nitro Phthalic Anhydride, Cobalt salt and Urea with Chloromethylpolyestyrene as a Heterogenous, Reusable and Efficient Catalyst Mohammad Ali Zolfigol 2, Ali Reza Pourali 1, Sami Sajjadifar 3,4 and Shohreh Farahmand 1,2,4 1Faculty of Chemistry, Bu-Ali Sina University, Hamedan, P.O. Box 6517838683, Iran 2School of Chemistry, Damghan University, Damghan, Iran 3Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran 4Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran _____________________________________________________________________________________________ ABSTRACT 3-Nitrophthalic anhydride was reacted with urea and cobalt salt in nitrobenzene under N 2 at 185°C and cobalt- tetraanitrophthalocyanine (CoTNP) was produced. Cobalt-tetraaminophthalocyanine (CoTAP) was produced by reduction of CoTNP caused by Sodium borohydride under N 2(g). CoTAP and chloromethylpolystyrene was refluxed in nitrobenzene or DMF at 180 oC for 12h. The mixture was cooled down to reach the room temperature and then solvent removed and the resulting precipitate was washed with water to remove excess CoTAP, and dried it to get a light green solid (CoTAP-linked-polymer). Kaywords Phthalocyanines, Cobaltetraminophthalocyanine, CoTAP ,Phthalocyanines linked polymer. _____________________________________________________________________________________________ INTRODUCTION Phthalocyanines are of interest not only as model compounds for the biologically important porphyrins but also because the intensely colored metal complexes are of commercial importance as dyes and pigments [1], the copper derivatives being an important blue pigment [2].
    [Show full text]
  • Resorcinol and Sulfonates Criteria
    02/22/13 COMMONWEALTH OF PENNSYLVANIA DEPARTMENT OF ENVIRONMENTAL PROTECTION BUREAU OF POINT AND NON-POINT SOURCE MANAGEMENT RATIONALE FOR THE DEVELOPMENT OF AMBIENT WATER QUALITY CRITERIA RESORCINOL & SULFONIC ACID COMPOUNDS (Revised February 2012) (Revised February 2013) Introduction: Beazer East, Inc. (Beazer) implemented environmental investigations and remediation at sites in Butler and Armstrong Counties, Pennsylvania in cooperation with the Department of Environmental Protection (Department) and United States Environmental Protection Agency (U.S. EPA). These sites are located within an area approximately 60 square miles in size that has been designated by the Department under the Hazardous Sites Cleanup Act (HSCA) as the “Bear Creek Area Chemical Site” (BCACS). The Department has determined that environmental media (i.e. soil and groundwater) within the BCACS have been impacted by sulfonate (sulfonic acid) compounds and resorcinol and other hazardous substances. The sulfonic acid compounds include meta-benzene disulfonic acid (m-BDSA), benzene monosulfonic acid (BSA), p-phenol sulfonic acid (p-PSA). Currently, with respect to surface water, there are no ambient water quality criteria for the sulfonic acids or resorcinol, which are needed to evaluate the environmental clean-up objectives and progress within the BCACS. EPA and Department Review Aquatic Life Water Quality Criteria Developed by AMEC: Because water quality criteria had not been developed for the sulfonic acids or resorcinol by either the Department or the U.S. EPA, AMEC Earth & Environmental (AMEC) used U.S. EPA's national guidelines to develop aquatic life water quality criteria (Stephan, et al., 1985) in accordance with 25 Pa. Code § 16.22. (AMEC. April 2008).
    [Show full text]
  • Recommended Methods for the Identification and Analysis Of
    Vienna International Centre, P.O. Box 500, 1400 Vienna, Austria Tel: (+43-1) 26060-0, Fax: (+43-1) 26060-5866, www.unodc.org RECOMMENDED METHODS FOR THE IDENTIFICATION AND ANALYSIS OF AMPHETAMINE, METHAMPHETAMINE AND THEIR RING-SUBSTITUTED ANALOGUES IN SEIZED MATERIALS (revised and updated) MANUAL FOR USE BY NATIONAL DRUG TESTING LABORATORIES Laboratory and Scientific Section United Nations Office on Drugs and Crime Vienna RECOMMENDED METHODS FOR THE IDENTIFICATION AND ANALYSIS OF AMPHETAMINE, METHAMPHETAMINE AND THEIR RING-SUBSTITUTED ANALOGUES IN SEIZED MATERIALS (revised and updated) MANUAL FOR USE BY NATIONAL DRUG TESTING LABORATORIES UNITED NATIONS New York, 2006 Note Mention of company names and commercial products does not imply the endorse- ment of the United Nations. This publication has not been formally edited. ST/NAR/34 UNITED NATIONS PUBLICATION Sales No. E.06.XI.1 ISBN 92-1-148208-9 Acknowledgements UNODC’s Laboratory and Scientific Section wishes to express its thanks to the experts who participated in the Consultative Meeting on “The Review of Methods for the Identification and Analysis of Amphetamine-type Stimulants (ATS) and Their Ring-substituted Analogues in Seized Material” for their contribution to the contents of this manual. Ms. Rosa Alis Rodríguez, Laboratorio de Drogas y Sanidad de Baleares, Palma de Mallorca, Spain Dr. Hans Bergkvist, SKL—National Laboratory of Forensic Science, Linköping, Sweden Ms. Warank Boonchuay, Division of Narcotics Analysis, Department of Medical Sciences, Ministry of Public Health, Nonthaburi, Thailand Dr. Rainer Dahlenburg, Bundeskriminalamt/KT34, Wiesbaden, Germany Mr. Adrian V. Kemmenoe, The Forensic Science Service, Birmingham Laboratory, Birmingham, United Kingdom Dr. Tohru Kishi, National Research Institute of Police Science, Chiba, Japan Dr.
    [Show full text]