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(12) United States Patent (10) Patent No.: US 6,541,667 B1 Erdman (45) Date of Patent: Apr

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(12) United States Patent (10) Patent No.: US 6,541,667 B1 Erdman (45) Date of Patent: Apr USOO6541667B1 (12) United States Patent (10) Patent No.: US 6,541,667 B1 Erdman (45) Date of Patent: Apr. 1, 2003 (54) METHODS FOR PREPARATION OF OTHER PUBLICATIONS THOAMIDES Can. J. Chem., 63, (month unavailable) 1985, Khamis A. (75) Inventor: David T. Erdman, Liberty, MO (US) Abbas and John T. Edward, pp. 3075-3078, Effects of varying solvents and of the addition of sulfur on the rate of (73) Assignee: Bayer Corporation, Pittsburgh, PA thiohydrolysis of aromatic nitriles. (US) * cited by examiner (*) Notice: Subject to any disclaimer, the term of this Primary Examiner Peter O'Sullivan patent is extended or adjusted under 35 (74) Attorney, Agent, or Firm-Joseph C. Gil; Richard E. L. U.S.C. 154(b) by 0 days. Henderson (21) Appl. No.: 10/023,359 (57) ABSTRACT (22) Filed: Dec.e --17, is 2001 A process for preparing a thioamide of the formula (I) (51) Int. Cl." ...................... C07C327/48; CO7D 249/12 (I) (52) U.S. Cl. ....................................... 564/74; 548/263.2 S (58) Field of Search .......................... 564/74; 548/263.2 us R NH2 (56) References Cited U.S. PATENT DOCUMENTS wherein R is an aryl or a heteroaryl radical includes the Step of mixing a nitrile of the formula (II) 4,618,416 A 10/1986 Levesque et al. ........... 209/166 5,475,115 A 12/1995 Linker et al. ............ 548/263.2 R-CN (II) 5,639,891 A 6/1997 Linker et al. ............ 548/264.2 2. A 3. al - - - - - - - - - - - - $43, wherein R is an aryl or a heteroaryl radical with an aqueous ... .36 E. ... solution comprising a sulfide and water. 5,945,436 A 8/1999 Lai et al. .................... 514/357 6,077,813 A 6/2000 Linker et al. 21 Claims, No Drawings US 6,541,667 B1 1 2 METHODS FOR PREPARATION OF It is a further object of the present invention to provide THOAMIDES processes for the preparation of thioamides which do not require high preSSures. It is another object of the present invention to provide FIELD OF THE INVENTION processes for the preparation of thioamides which do not This invention relates to processes for preparing thioam require the use of and/or generate large quantities of hydro ides. More particularly, the invention relates to proceSS for gen Sulfide gas. preparing a thioamide of the formula (I): These and additional objects are provided by the pro ceSSes of the present invention. (I) 1O S In accordance with one aspect of the invention there are provided processes for preparing a thioamide of the formula R ul NH2 (I): 15 (I) wherein R is an aryl or a heteroaryl radical. The proceSS S includes the Step of mixing a nitrile with an aqueous Solution comprising a Sulfide and water. R l NH2 BACKGROUND OF THE INVENTION Thioamides may be used as fungicides, herbicides or as wherein R is an aryl or a heteroaryl radical, comprising the intermediates in the Synthesis of thiazoles. Thioamides may step of mixing a nitrile of the formula (II): also be employed as intermediates for preparing pharma ceuticals and crop protection agents. R-CN (II) Abbas and Edward, Can. J. Chem., 63:3075-3078 (1985) 25 wherein R is an aryl or a heteroaryl radical, with an aqueous teach that thioamides may be prepared from nitriles by Solution comprising a Sulfide and water. heating under preSSure with an alcoholic Solution of an alkali-metal hydroSulfide or an ammonium or Substituted In accordance with another aspect of the invention there ammonium hydrosulfide. Abbas and Edward also teach that are provided processes for preparing a thioamide of the thioamides may be prepared by bubbling hydrogen Sulfide formula (I): through Solutions of Substituted benzonitriles in pyridine (I) containing triethylamine. S Levesque et al., U.S. Pat. No. 4,618,416, teach thioamides can be prepared by dissolving a thioester into a Solvent and ul adding amine. 35 R NH2 Linker et al., U.S. Pat. Nos. 5,475,115, 5,639,891 and 5,739,349, teach that triazolinethiones can be prepared by wherein R represents an aryl or a heteroaryl radical, com reacting carboxylic acids with alkylthiosemicarbazides. prising the Step of reacting under pH controlled conditions Linker et al., U.S. Pat. No. 6,077,813, disclose Substituted a nitrile of the formula (II): aromatic thiocarboxcylic acid amides and their use as her 40 bicides. Linker et al. teach the Substituted aromatic thiocar R-CN (II) boxcylic acid amides are prepared by, reacting Substituted aromatic nitriles with hydrogen sulfide (HS) or with thio wherein R represents an aryl or a heteroaryl radical, with a acetamide. compound Selected from the group consisting of Sodium 45 hydrogen Sulfide, potassium hydrogen Sulfide, ammonium Jackson et al., U.S. Pat. No. 5,723,663, disclose a process Sulfide, disodium hydrogen Sulfide, dipotassium hydrogen for preparing an aliphatic thioamide which entails reacting Sulfide, and combinations thereof. an aliphatic nitrile with hydrogen Sulfide. The processes of the invention are advantageous in that Lai et al., U.S. Pat. No. 5,945,436, teach thioamides can the proceSS can occur in the presence of water, and in that be prepared by treating a nitrile in an inert Solvent with a 50 handling of large quantities of hydrogen Sulfide gas is Steady Stream on hydrogen Sulfide gas, catalyzed by a avoided. Secondary amine. The processes of the invention are advantageous in that Unfortunately, many of the prior art processes for the the proceSS can occur without the need for high pressures. preparation of thioamides require the use of large amounts These and additional aspects, objects and advantages of of hydrogen Sulfide gas, and thus raise concerns regarding 55 the invention are more fully described in the following Safety and/or difficulty of handling the gas. Many prior art detailed description. processes require Solvents Such as dry ethanol or pyridine, and the presence of water adversely affects the reaction. DETAILED DESCRIPTION Other prior art processes require that the process occur under high pressure. Thus there is a need for improved methods of 60 Processes in accordance with the present invention com preparing thioamides, particularly methods which do not prise the step of mixing a nitrile of the formula (II): require organic amines or large amounts of hydrogen Sulfide gaS. R-CN (II) SUMMARY OF THE INVENTION 65 wherein R is an aryl or a heteroaryl radical, with an aqueous Accordingly, it is an object of the present invention to Solution comprising a Sulfide and water to obtain a thioam obviate problems of the prior art. ide of the formula (I): US 6,541,667 B1 4 cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, (I) cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalky S lalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groupS and optionally 1 to 4 carbon atoms in R ul NH2 the alkyl groups, or unsubstituted or nitro-, cyano-, carboxyl-, halogen-, C-alkyl-, C-a-halogenoalkyl-, C-4- alkyloxy-, Ca-halogenoalkyloxy- and/or C-alkoxy wherein R represents an aryl radical or a heteroaryl radical. carbonyl-Substituted phenyl, phenyloxy, phenyl-C1-4-alkyl, While not being bound by theory, it is believed that the phenyl-C-alkoxy, phenyloxycarbonyl or phenyl-C- nitrile reacts with a first Sulfide to form a thioamide Salt, and alkoxycarbonyl, (in each case optionally totally or partially that the thioamide Salt deprotonates a Second Sulfide and hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, generates NaS. The reaction is believed to be as set forth in furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, Reaction Sequence 1, below: oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, S Na S pyrazolyl-C-alkyl, furyl-C-alkyl, thienyl-C-alkyl, NaSH / NaSH M 15 Oxazolyl-C-alkyl, isoxazole-C-alkyl, thiazole-C- R-CN -- R-C -> R-C V alkyl, pyridinyl-C-alkyl, pyrimidinyl-C-alkyl, pyra NH NH2 Zolylmethoxy or furylmethoxy, or represents perhydropyra nylmethoxy or pyridylmethoxy. The aryl or heteroaryl radical may be substituted with 2 The reaction can occur in the absence of added acid, however, the slow addition of acid to the mixture of nitrile, moieties which together form an alkanediyl or alkenediyl Sulfide and water is believed to assist in driving the reaction group having in each case up to 4 carbon atoms which to completion. optionally contains at the beginning (or end) or within the The aryl and heteroaryl radical contain from about 5 to hydrocarbon chain an oxygen atom, a Sulphur atom, an SO about 7, preferably from about 5 to about 6, atoms in the ring group, an NH group, an N-C-alkyl group, a carbonyl moiety. AS used herein, "heteroaryl radical” refers to an 25 group and/or a thiocarbonyl group. Further, the aryl or aromatic ring comprising at least one ring atom which is heteroaryl radical may be Substituted with a monocyclic or other than carbon, Such as a ring comprising a Sulfur, oxygen bicyclic, Saturated or unsaturated heterocyclyl, heterocycly or nitrogen atom. AS used herein, “aryl radical' is intended lamino or heterocyclylimino having in each case 2 to 6 to include Substituted and unsubstituted aryl radicals, and carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic “heteroaryl radical' is intended to include substituted and ring System, which optionally contains an oxygen atom or unsubstituted heteroaryl radicals. Suitable substituents Sulphur atom and from Zero to three, in one embodiment one include, but are not limited to, halogen, hydroxyl, alkyl, to three, Substituents Selected from the group consisting of alkenyl, alkinyl, alkoxy, aryl, aryloxy, alkylsulphonyl, CO-, -CS-, -SO- and/or -SO-, and which is arylsulphonyl, alkanediyl,
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