GB1355802A - Amido or imido sulphenamides - Google Patents

Abstract

1355802 Acylamino sulphides IMPERIAL CHEMICAL INDUSTRIES Ltd 21 May 1971 [12 Aug 1970] 38874/70 Heading C2C The invention comprises compounds of the formula in which X is CO or a direct link, R 1 and R 2 are alkyl, aralkyl or optionally substituted cycloalkyl or aryl groups, or taken together represent an alkylene, cycloalkenylene or optionally substituted alkenylene or arylene radical, R 3 is hydrogen or an alkyl, aralkyl or optionally substituted cycloalkyl or aryl group, and R 4 is an alkyl, aralkyl or optionally substituted cycloalkyl or aryl group, or R 3 and R 4 together with the N atom represent (i) a saturated heterocyclic radical containing nitrogen and optionally containing a single O, S or N atom as a second hetero atom, or (ii) a group of the formulae and their production by reacting R 1 CON(XR 2 ).- SY (where Y is Cl or Br) with R 3 R 4 NH; or (when R 3 is not hydrogen and X is CO) by reacting R 3 R 4 NSY with R 1 CONHCOR 2 in the presence of an acid binding agent, or with an alkali metal salt of such an imide. Specified substituents on cycloalkyl groups are methyl groups, and, on aryl groups (e.g. phenyl or naphthyl) are methyl, ethyl, halogen, NO 2 , alkoxy and alkoxycarbonyl. Examples prepare N-morpholino-N<SP>1</SP>-caprolactyl sulphide, N-(4-methylpiperidino)-N<SP>1</SP>-succinimidyl sulphide, N- morpholino-N<SP>1</SP>-phthalimidyl sulphide, N-piperidino-N<SP>1</SP>-caprolactyl sulphide, N-t-butylamino- N<SP>1</SP>-caprolactyl sulphide, and N,N<SP>1</SP>-bis-(N<SP>11</SP>- caprolactylthio)-p-phenylenediamine. Other starting materials are also listed. The compounds are used in the vulcanization of rubber.