Preparation of n-cyclohexyl-2-benzothiazole sulfenamide

Claim 1

IN A METHOD FOR THE PREPARATION OF N-CYCLOHEXYL-2BENZOTHIAZOLESULFENAMIDE IN WHICH CYCLOHEXYLAMINE IS CONVERTED TO N-CHLOROCYCLOHEXYLAMINE BY REACTION OF CYCLOHEXYLAMINE WITH AN AQUEOUS SOLUTION OF AN ALKALI METAL HYPOCHLORITE, AND THE SO-FORMED N-CHLOROCYCLOHYXYLAMINE IS REACTED IN AN ORGANIC SOLVENT WITH A BENZOTHIAZOLE DERIVATIVE SELECTED FROM THE GROUP CONSISTING OF 2-MERCAPTOBENZOTHIAZOLE AND 2,2''-DIBENZOTHIAZYL DISULFIDE IN THE PRESENCE OF A HYDROGEN CHLORIDE ACCEPTOR, THE BY-PRODUCT HYDROCHLORIDE IS REMOVED AND THE SOLVENT IS DISTILLED FROM THE RESIDUE TO OBTAIN THE PRODUCT SULFENAMIDE, THE IMPROVEMENT WHICH COMPRISES: DISSOLVING THE CYCLOHEXYLAMINE IN AN INERT, WATER-IMMISCIBLE ORGANIC SOLVENT, ADDING THERETO SUFFICIENT WATER TO FORM A DUAL-PHASE SYSTEM OF WATER IN CONTACT WITH THE ORGANIC SOLVENT WHEREIN THE WATER: ORGANIC SOLVENT RATIO IS FROM ABOUT 1:5 TO ABOUT 1:12; ADDING THERETO AN AQUEOUS SOLUTION OF SAID ALKALI METAL HYDPOCHLORITE; DURING SAID ADDITION, AGITATING THE RESULTING MIXTURE SUFFICIENTLY WELL TO FORM A DUAL-PHASE MEDIUM IN WHICH SAID ORGANIC SOLVENT SOLUTION IS DISPERSED UNDER AGITATION AND TAINING THE RESULTING DISPERSION UNDER AGITATION AND AT AN AVERAGE TEMPERATURE IN THE RANGE OF FROM ABOUT MINUS 10* TO ABOUT 10*C., UNTIL THE RESULTING CHLORINATION OF THE CYCLOHEXYLAMINE SUBSTANTIALLY CEASES; THEN STOPPING THE AGITATION, WHEREBY THE MIXTURE SEPARATES INTO AN AQUEOUS LAYER AND AN ORGANIC LAYER, N-CHLOROCYCLOHEXYLAMINE BEING DISSOLVED IN SAID ORGANIC LAYER; COLLECTING SAID ORGANIC LAYER AND WITHOUT ISOLATION OF THE N-CHLOROCYCLOHEXYLAMINE REACTING THEREWITH, IN SAID SOLUTION, SAID BENZOTHIAZOLE DERIVATIVE.