Illustrated Glossary of Organic Chemistry

Transamidation: The conversion of one amide into another amide. The amide nitrogen is changed,while retaining the acyl group of the starting molecule.

	+	(CH3)2NH			+	NH3
Acetamide		Dimethylamine		N,N-dimethylacetamide		Ammonia

In this transamidation example, acetamide (a primary amide) is converted into N,N-dimethylacetamide (a tertiary amide) by a nucleophilic carbonyl substitution reaction with dimethylamine (a secondary amine) as the nucleophile. Note that the acetyl group is retained in this transformation. Because the two amides have roughly equal stability, a large excess of dimethylamine must be used to cause the equilibrium to shift to the tertiary amide (due to Le Chatelier's principle).