GB602558A - Manufacture of aromatic acyl-sulphonamides - Google Patents

Abstract

Aromatic acyl-sulphonamides having the general formula R1.SO2.NH.CO.R2 (in which R1 is a benzene radical substituted by alkyl, alkoxy and/or alkylmercapto groups and R2 is a benzene radical substituted by alkyl, alkoxy, alkylmercapto groups and/or halogen) are made by reacting sulphonamides of the general formula R1.SO2.NH2 with substituted aromatic carboxylic acids of the general formula R2.COOH or their functional derivatives. In a modification, the same products are obtained by reacting benzene sulphohalides of the formula R1.SO2.Hal with salts of amides of substituted aromatic acids of the formula R1.COOH, in which R1 and R2 have the same meaning as before. In examples: (1) N-(31,41-dimethyl - benzoyl) - 3,4 - dimethylbenzene sulphonamide is made by heating 3,4-dimethyl-benzene sulphonamide and 3,4-dimethylbenzoyl chloride in pyridine- and similarly, the N-(31,41-dimethylbenzoyl) -4 - ethyl - (or -4-methoxy-, or -3-ethoxy-)-benzene sulphonamide is obtained from 4-ethyl-(or 4-methoxy-, or 3-ethoxy-)-benzene sulphonamide-; (2) N-(31,41-dimethylbenzoyl)-3,4-dimethylbenzene sulphonamide is made by heating 3,4-dimethylbenzene sulphonamide and 3,4-dimethylbenzoic acid with phosphorus pentoxide in chlorobenzene; (3) N-(4-isoamyloxy - benzoyl) - durene sulphonamide is made by heating durene sulphonamide and 4-isoamyloxy-benzoyl chloride in dimethylaniline, similarly, N-(3- or 4-methoxybenzoyl)-durene sulphonamide is obtained from durene sulphonamide and m- or p-methoxybenzoyl chloride (or bromide); (4) N-(2,5-dichlorobenzoyl)-p-toluene sulphonamide is made by heating p-toluene sulphonamide and 2,5-dichlorobenzoyl chloride with aluminium chloride in nitrobenzene, similarly, N - (4 - methylthio- or 3 - ethylthio - benzoyl)-p-toluene sulphonamide may be prepared using 4-methylthio- or 3-ethylthio-benzoyl chloride; and (5) N-(2,5-dichlorobenzoyl)-p-toluene sulphonamide is made from the sodium salt of 2,5-dichlorobenzoic acid amide and p-toluene sulphochloride in xylene. Other suitable substituted benzene sulphonamides and substituted benzene carboxylic acids are specified.