GB550446A - Process for the preparation of sulphenamido and sulphonamido derivatives of heterocyclic compounds - Google Patents

Abstract

550,446. Sulphenamido and sulphonamido compounds. MAY & BAKER, Ltd., and BARBER, H. J. June 4, 1941, No. 7070. [Class 2 (iii)] Benzene sulphenyl halides having in the pposition a halogen atom or a nitrogen-containing group capable of conversion into an amino group are reacted with pyridine or thiazole compounds containing an amino group to give sulphonamido compounds which, on oxidation, yield sulphonamido-pyridine and -thiazole compounds. The reaction with the sulphenyl halide is effected under alkaline conditions and in the absence of a hydroxylic solvent, whilst the oxidation takes place in an alkaline medium. Nitrogen-containing groups mentioned are arylamino, nitro, azo and hydrazo groups. The products may be converted into the corresponding p-amino compounds which are useful therapeutically. According to the examples (1) p-nitrobenzenesulphenyl chloride, prepared from p : p<SP>1</SP>-dinitrodiphenyldisulphide is treated with excess 2 - aminopyridine in ethereal solution and the resulting 2 - p - nitrobenzenesulphenamido-pyridine oxidized with aqueous potassium permanganate ; (2) acetanilido - p - sulphenyl bromide, obtained from acetanilido - p : p'-disulphide, is reacted with 2 - aminopyridine in ether and. then oxidized in acetone solution by addition of aqueous potassium permanganate containing a little caustic soda to give 2 - p - acetylaminobenzenesulphonamido-pyridine ; (3) p-nitrobenzenesulphenyl chloride is reacted in chloroform solution with excess of 2-aminothiazole to form 2 - p - nitrobenzenesulphenamido-thiazole; (4) p-nitrobenzenesulphenyl chloride is treated in ether-carbon tetrachloride with 2 - aminobenzthiazole in presence of a little sodium carbonate and yields 2- p - nitrobenzenesulphenamido-benzthiazole. Specifications 379,683, 512,145, 551,206 and 551,681 are referred to ; the Provisional Specification also refers to Specification 517,272.