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Amines attack acyl chlorides to give amides

The mechanism is very similar to attack by alcohol:


Notice that two equivalents of ammonia are required.

The attack can be done by other amines, not just ammonia:


While ammonia is easy to add in excess, protonating amines can be wasteful if the amine is rare or expensive. A base such as NaOH could deprotonate the amines. But OH- is itself a nucleophile. The solution is to use two separate phases:


This two-phase strategy is called the Schotten-Bauman synthesis.

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