34.1.2—Amide formation from amines

Ammonia or an amine reacts with an acyl chloride at room temperature to form an amide. The nitrogen nucleophile attacks the carbonyl carbon, chloride leaves, and HCl is produced.

Ammonia gives a primary amide; a primary amine gives an N-substituted secondary amide. A second equivalent of amine or another base can remove the HCl.

CH₃COCl + 2NH₃ → CH₃CONH₂ + NH₄Cl overall. With methylamine, the product is N-methylacetamide rather than acetamide.

Do not call this simple acid–base neutralisation or write an alcohol product; the nitrogen remains attached to the acyl carbon.