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Experiment 1: Synthesis of Acetamides from Aniline and Substituted Anilines

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Experiment 1: Synthesis of Acetamides from Aniline and Substituted Anilines Chem 216 S11 Notes - Dr. Masato Koreeda Date: May 3, 2011 Topic: __Experiment 1____ page 1 of 2. Experiment 1: Synthesis of Acetamides from Aniline and Substituted Anilines Many of the acetylated [CH3–C(=O)-] derivatives of aromatic amines (aka anilines) and phenols are pharmacologically important compounds. Some of these exhibit distinct analgesic activity. Two of the most representative examples are: H HO O N CH3 O CH3 O HO O acetaminophen (Tylenol) acetylsalicylic acid (Aspirin) ======================================================================= The reaction to be carried out in this experiment is: Acetylation of aniline δ- H3C δ+ O acetic O O anhydride H N CH3 N H (electrophile) HO O CH3 + H O CH3 acetanilide acetic acid aniline (nucleophile) Both aniline and acetic anhydride are somewhat viscous liquids. So, simply mixing them together does not result in the efficient formation of acetanilide. Therefore, a solvent (in this case water) is used to dissolve and evenly disperse two reactants in it. R R R Note: O + N R" N R" N CH R' R' R' 3 CH3 - O O O acetyl group amide The amide N is usually not nucleophilic acetamide because of a significant contribution of this resonance form. Reaction mechanism: δ- H H3C H H H3C δ+ O H N O H O N O CH3 O O N + O O H CH3 O CH3 CH3 pKa ~ -5 3 O CH3 tetrahedral (sp ) intermediate B (including ) O H N CH3 O acetanilide Chem 216 S11 Notes - Dr. Masato Koreeda Date: May 3, 2011 Topic: __Experiment 1____ page 2 of 2. Additional comments on the reaction mechanism: 1. Aniline is a strong nucleophile (much stronger than water). 2. Acetic anhydride is a relatively unstable reagent, but does not react with water that easily. 3. H H N O A direct substitution process at the C=O carbon does not take place. O No direct S 2 reaction at the C=O carbon is known. This is not feasible H3C N O on the basis of the orbital consideration. CH3 Experimental procedure: Aniline is not soluble in water; so 1 mol. equiv of conc. HCl (37% HCl by weight in water) is added in order to dissolve the aniline in water. add 1 mol equiv add 1 mol equiv aniline of conc HCl of acetic anhydride H2O H2O + - H2O + - PhNH3 Cl , acetic anhydride PhNH3 Cl Erlenmeyer flask (still all dissolved in H2O) Don't use a beaker! (all dissolved) homogeneous solution no reaction yet! add 1.2 mol equiv of - + NaCl, acetic acid and H3C O Na - CH3C(=O)O dissolved O By the action of sodium acetate, (sodium acetate) in H2O a small amount of free - weak base aniline (PhNH2) is regenrated. o o o Free aniline has virtually no water solubility. o o o o ooo o o o o o o o o But before aniline comes out of the H2O solution, H2O acetanilide as white it quickly collides (i.e., reacts) with acetic + precipitates (collect by anhydride dissolved in H2O. As soon as the Mostly PhNH3 suction filtration) acetamide product (acetanilide) is formed, and NaCl, acetic anhydride, and it will precipitate out of the H O solution and - 2 CH3C(=O)O more PhNH + gets converted to free aniline.... 3 (dissolved in H2O) Questions: (1) What would happen if the order of additions of acetic anhydride and sodium acetate is reversed? (2) What would be the outcome if 1 mol equiv of NaOH is used instead of sodium acetate? (3) What would you have to do in order to dissolve p-nitroaniline into water by adding conc. HCl? The pKa of the conjugate acid of p-nitroaniline is 1.00 (see the note on pKa). .
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