GB584693A - Preparation of therapeutically useful sulphones - Google Patents

Abstract

Compounds having the formula <FORM:0584693/IV/1> where Z is H, Cl, Br, NO2 or NH-acyl and R1 is <FORM:0584693/IV/2> , or <FORM:0584693/IV/3> or <FORM:0584693/IV/4> -COOH are obtained by heating a phenyl sulphenyl compound, e.g. chloride or alkanolate with a 2-amino-thiazole in the presence of a acylating agent at about 85-90 DEG C. The sulphide compounds thus obtained may be oxidized to the corresponding sulphones and the substituents Z, R1 and R2 converted. In examples: (1a) acetic anhydride is added to p-nitrophenyl sulphenyl chloride and 2-aminothiazole in glacial acetic acid to obtain 2-acetylamino-thiazolyl-5-41-nitrophenyl-sulphide; (1b) the product of (1a) is oxidized by means of concentrated hydrogen peroxide in glacial acetic acid to the corresponding sulphone; (1c) the sulphone of (1b) is deacetylated with hydrochloric acid; (1d) the sulphone of (1b) is reduced by means of ammonium chloride and iron to 2,41-diamino-thiazolyl-5-phenyl sulphone; (2) the sulphone of (1b) is reduced and then deacetylated to obtain 2,41-diaminothiazolyl-5-41-nitrophenyl sulphone; (3a) 2-succinylamino - thiazolyl - 5 - 41 - nitrophenyl sulphide is obtained using the method of (1a), but replacing the acetic anhydride with succinic anhydride and oxidized to the corresponding sulphone as in (1b); (3b) 2-succinylaminothiazolyl-5-41-nitrophenyl sulphone is reduced as in (1d) to the corresponding amino compound; (4) 2 - crotonylamino - thiazolyl - 5 - 41 - amino - phenyl sulphone is obtained by the method of example 3 except using crotonic anhydride; (5) the reaction product of p-nitrobenzene sulphenyl chloride and an alkali metal alkanolate is condensed with 2-amino-sulphathiazole and the product re-arranged as in (1a) to obtain 2 - acetylamino - thiazolyl - 5 - 41 - nitro - phenyl sulphide; (6) 2-acetylamino-thiazolyl-5-phenyl sulphide is obtained from p-nitro-benzene sulphenyl chloride by the method of (1a); (7) 2 - acetylamino - thiazolyl - 5 - 41 - chlorophenyl sulphide is obtained from 4-chloro-benzene sulphenyl chloride by the method of (1a); (8) 2,41-diacetylamino-thiazolyl-5-phenyl sulphide is obtained from p-acetylamino-benzene sulphenyl chloride by the method of (1a).