GB874519A - The production of azathiacyclohexane-4,4-dioxide and derivatives thereof - Google Patents

Abstract

1-Aza-4-thiacyclohexane-4,4-dioxide or a derivative thereof substituted on nitrogen and/or one or more carbon atoms is prepared by reacting at elevated temperature bis (b -hydroxyethyl)-sulphone or oxathiacyclohexane-4,4-dioxide, or one of their derivatives substituted on carbon, with ammonia or an aliphatic, cycloaliphatic or araliphatic amine containing at least one primary amino group or with hydrazine or a hydrazine substituted on one of the NH2-groups only, preferably in water or an organic solvent. Temperatures of 100-300 DEG C. are mentioned and elevated pressures, e.g. autogenic, are preferred. The sulphone starting material may be used without isolation after its preparation by oxidising the corresponding thioether. The amine starting material may be substituted, e.g. by further amino groups, ester or nitrile groups, or the carbon chain may be interrupted by hetero atoms, e.g. N or O. Certain azathiacyclohexane dioxides are claimed per se, viz: (i) compounds of formula <FORM:0874519/IV (b)/1> where R1 is hydrogen or alkyl, R2 is hydrogen or C1-4 alkyl, R3 is hydrogen, C1-4 alkyl, phenyl, methylphenyl or 2-methoxy-5-methylphenyl, and n is 2 to 6 inclusive; (ii) N-amino-azathia-cyclohexane-4,4-dioxide and (iii) 2,6-dimethyl-azathia-cyclohexane-4,4-dioxide. Compounds prepared in examples but not claimed per se are: azathiacyclohexane-4,4-dioxide, N-methyl-, N-hydroxyethyl-, N-benzyl-, N-2-ethylhexyl, N-anilino- and N-cyclohexyl-azathiacyclohexane -4,4- dioxides, and hexamethylene-bis(azathiacyclohexane-4, 4-dioxide).