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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