The formation and hydrolysis of substituted N-chloro-N-methylbenzamides in aqueous alkali

Abstract

The reaction of a series of o-, m-, and p-substituted N-methylbenzamides with hypochlorite ion to form the corresponding N-chloro-compounds, and the hydrolysis of these derivatives in aqueous alkaline solution have been examined using an automatic recording titrator on pH-stat operation. The two reactions are the halves of an equilibrium process. It is postulated that hydrolysis takes place by base-catalysed formation of an imino-hypochlorite intermediate followed by its rate-determining reaction with hydroxide ion. Chlorination will then proceed by the reverse of this process such that cleavage of the N–H bond is rate-determining.