Kinetics of the chlorination of secondary amines by N‐chlorosuccinimide

The chlorinations of dimethylamine, diethylamine, methylethanolamine, ethylethanolamine and diethanolamine by N‐chlorosuccinimide have been found to be equilibrium reactions of order one with respect to both N‐chlorosuccinimide and amine in the forward direction and of order one with respect to succinimide and the resulting N‐chloramine in the other. These results are explained by postulating a mechanism in which the rate controlling step consists in direct exchange of positive chlorine between the N‐chlorosuccinimide and the amine.