Improvements in and relating to the manufacture of sulphonamido compounds

摘要

551,205. Aryl sulphenamides and sulphonamides. MANCHESTER OXIDE CO., Ltd., BANN, B., KRUB, P., WHEELER, D. E., TAYLOR, W., and GLADDING, G. April 29, 1941, Nos. 7282/42 and 7283/42 [both divided out of 553,269] [Class 2 (iii)] )] Benzenesulphonamidoguanidines and p-substituted derivatives thereof are prepared by the oxidation of the corresponding sulphenamides, e.g. with alkali or alkaline earth metal permanganate or hypochlorite. The sulphenamides may be obtained by treating a diphenyldisulphide with chlorine in a non-aqueous medium and reacting the resulting sulphenyl chloride with guanidine or a substituted guanidine such as phenylguanidine ; the diphenyldisulphides may be prepared by heating with caustic alkali a thiocyanobenzene obtainable as described in Specifications 513,473 and 514,203. The sulphenamides may also be prepared by reacting a benzenesulphenyl ester with a guanidine. The substituent in the p-position is preferably a halogen atom or a nitrogencontaining group convertible into an amino group, e.g. an acylamino or nitro group, and the products may be converted into the amino compounds which are useful therapeutically. According to the examples, (1) benzenesulphenyl chloride, prepared by chlorinating diphenyldisulphide in chloroform, is reacted with guanidine nitrate in the presence of sodium ethoxide, and the resulting benzenesulphenylguanidine oxidised with aqueous potassium permanganate to benzenesulphonylguanidine ; (2) p-nitrobenzenesulphonylguanidine is prepared by chlorinating 4:41-dinitrodiphenyldisulphide in chloroform, converting the resulting p-nitrobenzenesulphenyl chloride into p-nitrobenzenesulphenic acid ethyl ester by treatment with sodium ethoxide, heating it with guanidine nitrate in the presence of sodium ethoxide and oxidising the p-nitrobenzenesulphenylguanidine so formed with potassium permanganate ; (3) p-aminobenzenesulphonylguanidine is obtained by treating p-nitrobenzenesulphenyl chloride with guanidine nitrate in presence of sodium ethoxide, oxidising the p-nitrobenzenesulphenylguanidine with aqueous potassium permanganate and reducing with ferrous hydroxide ; calcium permanganate solution may alternatively be used ; (4)p-aminobenzenesulphonylguanidine is also obtained by chlorinating 4:41-diacetyl-' diaminodiphenyldisulphide in chloroform, reacting the p-acetylaminobenzenesulphenyl chloride with guanidine nitrate, oxidising the sulphenylguanidine with potassium permanganate and hydrolysing the product; (5) pchlorobenzenesulphonylguanidine is prepared by chlorinating 4:41-dichlorodiphenyldisulphide, treating the p-chlorobenzenesulphenyl chloride with guanidine nitrate and oxidising the product with sodium hypochlorite solution ; the p-chloro group may be converted into amino by treatment with ammonia. Specification 379,683 also is referred to. The first Provisional Specification refers to the production of the naphthyl compounds.