Reactions of benzenesulfonohydrazides and benzenesulfonamides with hydrogen chloride or hydrogen bromide in acetic acid.
Benzenesulfonohydrazides capable of yielding a sulfinic acid intermediate by virtue of a basic nitrogen atom in the second position of the hydrazide moiety produced thiosulfonates when treated with 1 N hydrogen chloride in acetic acid and produced disulfides when treated with 1 N hydrogen bromide in the same solvent. In two cases, a crystalline mixture of P-nitrophenyl p-nitrobenzenethiosulfonate and bis(p-nitrophenyl) disulfide was isolated from the hydrogen chloride reactions. No reaction product was obtained from either the hydrogen chloride or hydrogen bromide reaction with benzenesulfonohydrazides that were unable to form a sulfinic acid intermediate. Reduction of benzenesulfonamides to disulfides appeared to be possible only with hydrogen bromide in acetic acid. No thiosulfonate was isolated from the treatments of benzenesulfonamides with 1 N hydrogen chloride in acetic acid. p-Nitrophenyl p-nitrobenzenethiosulfonate and p-bromophenyl p-bromobenzenethiosulfonate exhibited some antimicrobial activities against Gram-positive bacteria. The latter compound also showed analgesic properties in the phenylquinone test.
D000085:Acetates; D001419:Bacteria / Q000187:drug effects; D001965:Bromides; D055598:Chemical Phenomena; D002621:Chemistry; D006834:Hydrazines; D006851:Hydrochloric Acid; D010879:Piperazines; D013449:Sulfonamides; D013886:Thiosulfonic Acids / Q000138:chemical synthesis / Q000494:pharmacology
D000085:Acetates; D001965:Bromides; D006834:Hydrazines; D010879:Piperazines; D013449:Sulfonamides; D013886:Thiosulfonic Acids; D006851:Hydrochloric Acid