GB517421A - Manufacture of sulphur-containing organic compounds - Google Patents

Abstract

517,421. Sulphoxides and sulphones. ELLINGWORTH, S., ROSE, F. L., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. June 27, 1938, Nos. 19056/38 and 14768/39. [Class 2 (iii)] Sulphoxides and sulphones of the general formula where X indicates > S = O or > #S# and R1 and R2 are dissimilar aliphatic hydrocarbon radicals, or one of them but not both may be hydrogen are prepared by reacting a compound of the general formula where R2 is an aliphatic organic radical and Y is > S, > S = O, or < S # with an acid or acids of the formula R1 . COOH, where R1 is an aliphatic organic radical. In place of the acid a functional derivative thereof such as the anhydride, acid halide or ester may be used, and where necessary the central sulphur atom or sulphoxide grouping is oxidized to a sulphoxide or a sulphone grouping. The compounds possess chemotherapeutic action against streptococcal and pneumococcal infections. Oxidizing agents specified for the latter part of the process include hydrogen peroxide and chromic acid. In examples (1) 4-amino-4<1>-acetylaminodiphenyl sulphoxide, propionic acid and propionic anhydride are heated to 90‹C. for 15 minutes. On cooling water is added and crude 4-propionylamino- 4<1>-acetylamino-diphenyl sulphoxide separates as an oil. It is purified by recrystallization; (2) 4-amino-4<1>-acetylamino-diphenyl sulphide, propionic acid and propionic anhydride are heated as in example (1) to give 4-propionylamino-41-acetylamino-diphenyl sulphide. This. is oxidized with hydrogen peroxide in acetic acid solution to give 4-propionylamino-4<1>- acetylaminodiphenyl sulphone ; (3) 4-amino-41- acetylaminodiphenyl sulphide, propionyl chloride and crystallized sodium acetate are heated to 100‹C. for 15 minutes to form 4- propionylamino - 4 - acetylamino - diphenyl sulphide which is oxidized to the corresponding sulphone as described in example (2); (4) 4- amino - 4<1> - n - butylaminodiphenyl sulphide prepared by reducing 4-nitro-4<1>-n-butylaminodiphenyl sulphide, glacial acetic acid and acetic anhydride are heated together to give 4- acetylamino-4<1>-n-butylaminodiphenyl sulphide which is oxidized to the corresponding sulphone by hydrogen peroxide in acetic acid solution ; (5) The acetic acid in example (4) is replaced by propionic anhydride to give first 4-propionylamino - 4<1> - n - butylaminodiphenyl sulphide which is then oxidized as before to the corresponding sulphone ; (6) 4-propionylamino-4<1>- acetylaminodiphenyl sulphide prepared as in example (2) is dissolved in hot acetone and oxidized with aqueous hydrogen peroxide to 4-propionyl-amino-4<1>-acetylaminodiphenyl sulphoxide; (7) 4-amino-4<1>-formylaminodiphenyl sulphone, glacial acetic acid and acetic anhydride are heated together to give 4-acetylamino- 4<1>-formylaminodiphenyl sulphone. Specification 517,457 is referred to.