Preparation of N‐cyclohexylbenzothiazole‐2‐sulphenamide by oxidative condensation

Abstract It has been shown that in the preparation of N ‐cyclohexylbenzothiazole‐2‐sulphenamide by the reaction of 2‐mercaptobenzothiazole with cyclohexylamine in the presence of sodium hypochlorite, N ‐cyclohexyl‐benzothiazole‐2‐sulphonamide, sodium benzothiazole‐2‐sulphonate, benzothiazole‐2‐sulphonyl chloride, 2,2′‐dithiobisbenzothiazole, and probably sodium benzothiazole‐2‐sulphinate can be formed as by‐products, in amounts depending on pH, temperature and amount of amine used. Mechanisms are suggested for the reactions involved.