Carbamoyl chloride
A carbamoyl chloride is the functional group with the formula R2NC(O)Cl. 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 (m.p. −90 °C and b.p. 93 °C). Carbamoyl chlorides are used to prepare a number of pesticides, e.g. carbofuran and aldicarb.
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.
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 if the analogous reaction with alcohols:
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