Carbamoyl chloride


A carbamoyl chloride is the functional group with the formula R2NCCl. The parent carbamoyl chloride, H2NCOCl is unstable, but many N-substituted analogues are known. Most examples are moisture sensitive, colourless, and soluble in nonpolar organic solvents. An example is dimethylcarbamoyl chloride. Carbamoyl chlorides are used to prepare a number of pesticides, e.g. carbofuran and aldicarb.

Production and examples

Carbamoyl chlorides are prepared by the reaction of an amine with phosgene:
They also arise by the addition of hydrogen chloride to isocyanates:
In this way, carbamonyl chlorides can be prepared with N-H functionality.

Reactions

In a reaction that is typically avoided, hydrolysis of carbamoyl chlorides gives carbamic acids:
Owing to the influence of the amino group, these compounds are less hydrolytically sensitive than the usual acid chlorides.
A related but more useful reaction is the analogous reaction with alcohols: