Patent GB-598472-A (GB)
Title: Manufacture of para-aminobenzene sulphonacylamides
IPC: C07D261/16
Filed: 1944-11-03
Abstract: Para-aminobenzene sulphonacylamides of the general formula <FORM:0598472/IV/1> where R1 is a heterocyclic residue containing as substituents halogen, an alkyl residue, and/or an alkoxy alkylthio-residue, R2 represents hydrogen, alkyl or aralkyl and R3 represents hydrogen or alkyl are made by treating a sulphonamide of the benzene series, containing in the para position an amino group or a group which may be converted into an amino group by hydrolysis or reduction, with a carboxylic acid of the formula R1-COOH or with a functional derivative of such an acid.  In a modified process, a benzene sulpho-halide substituted in the para position with a group containing nitrogen and which is convertible by reduction or hydrolysis to an amino group, is reacted with a salt of an acid amide of the general formula R1-CO.NH2, where R1 has the meaning previously ascribed to it, giving the desired type of product. Suitable sulphonamides are those mentioned in the parent Specification and also the ureides, urethanes and amino alkylene sulphonic acids. Specified heterocyclic carboxylic acids are 2 : 5-dimethylpyrrole-3-carboxylic acid, 2 : 5-dimethylfurane-3-carboxylic acid, 5-tertiary-butyl-furane-2-carboxylic acid, 2 - methylfurane - 5 - carboxylic acid, 2 : 4 - dimethylfurane - 3 - carboxylic acid, 3-methyl-pyrazole-5-carboxylic acid, 5-methyl-isoxazole-3-carboxylic acid, 3-methylisoxazole-5-carboxylic acid, 3 : 5 - dimethylisoxazole-4-carboxylic acid, 4-methyl-thiazole-5-carboxylic acid, 2 - chloro - 4 - methylthiazole - 5 - carboxylic acid, 2 : 4 - dimethylthiazole - 5 - carboxylic acid, 6 - chloro - pyridine - 3 - carboxylic acid, 2 : 4 - dimethylpyridine-3-carboxylic acid, 6-methoxypyridine-3-carboxylic acid, 6-methylmercaptopyridine-3-carboxylic acid, 1 - ethyl - pyridone-(6)-3-carboxylic acid, 1-isobutylpyridone-(6)-3-carboxylic acid, 6 - methoxy - 2 : 4 - dimethylpyridine - 3 - carboxylic acid, 6-ethyl mercapto-2 : 4 - dimethyl - pyridine - 3 - carboxylic acid, 5 - methyl - pyrimidine - 4 - carboxylic acid, 5 - methylthiodiazole-(1 : 2 : 3)-4-carboxylic acid, 4 : 6 - dimethyl - pyrimidine - 2 - carboxylic acid, 3 : 6 - dimethyl - pyridazine - 4 - carboxylic acid, 3-methyl-oxdiazole-(1 : 2 : 4)-5-carboxylic acid, 2 - ethyl - pyrimidine - 4 - carboxylic acid, 5 : 6-dimethylpyrazine-3-carboxylic acid, 1-methylpyrrolidine-2-carboxylic acid, 2-methyl-benzthiazole - 7 - carboxylic acid, 5 - ethylthiodiazole-(1 : 3 : 4)-2-carboxylic acid, 2-methylpyridine-3-carboxylic acid, 2-methylpyridine-3-acetic acid, 2 : 6-dimethyl-4-chlorpyridine-3-carboxylic acid and 4 : 5 - dimethylpyridine - 3 - carboxylic acid.  These are made as described in the literature.  In examples: (I) para-aminobenzene-sulphon-3 : 5-dimethylisoxazole-4-carboxylic acid is prepared by the reaction of sodium para-nitrobenzene sulphonamide with 3 : 5-dimethylisoxazole-4-carboxylic acid chloride followed by reduction of the nitro group in an analogous manner; (II) 4-aminobenzene-sulphon-21 : 61-dimethyl-41-chloropyridine-31-carboxylic acid amide is prepared from 2 : 6-dimethyl-4-chloropyridine-3-carboxylic acid chloride and 4-acetylaminobenzene sulphonamide.  4-Ureido-aminobenzene - sulphon - 21 : 61 - dimethyl - 41 - chloropyridine-31-carboxylic acid amide and sodium benzene - sulphon - 21 : 61 - dimethyl - 41 - chlorpyridine-31-carboxylic acid amide 4-aminomethane sulphonate can be obtained in a similar manner; (III) 4-aminobenzene-sulphon-11-ethylpyridone-(61) -carboxylic acid amide is prepared from para-acetylaminobenzene sulphonamide and 1-ethylpyridone-(6)-3-carboxylic acid; (IV) 4 - aminobenzene - sulphon - 21 : 41 - dimethylcoumalic acid amide is prepared from 4-carbethoxy-aminobenzene sulphonamide and 2 : 4-dimethyl coumalic acid chloride; (V) 4-aminobenzene - sulphon - 51 - methylpyrimidine - (41)-carboxylic acid amide is prepared from para-nitrobenzene-sulphochloride and 5-methylpyrimidine-(4)-carboxylic acid amide; (VI) 4-aminobenzene-sulphon-21-61-dimethyl-41 -ethoxypyridine-31-carboxylic acid amide is prepared from 2 : 6-dimethyl-4-ethoxypyridine-3-carboxylic acid chloride and para nitrobenzene sulphonamide; (VII) 4-aminobenzene-sulphon-51 - tertiary - butylfurane - 21 - carboxylic acid is prepared from 5-tertiary-butylfurance-2-carboxylic acid chloride and para-nitrobenzene sulphonamide.  Specification 578,564 is referred to.