Login processing...

Trial ends in Request Full Access Tell Your Colleague About Jove

14.22: Preparation of Amides

JoVE Core
Organic Chemistry

A subscription to JoVE is required to view this content. Sign in or start your free trial.

Preparation of Amides

14.22: Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).

The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.

Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the final step, dicyclohexylurea departs to give an amide as the final product.


Alternatively, acid halides or acid anhydrides undergo aminolysis to form amides. The reaction requires two equivalents of ammonia or amines, where one equivalent acts as a nucleophile and the second functions as a base to give the substitution product. Interestingly, the best amide yield is obtained from highly reactive acid halides.

Similarly, esters undergo aminolysis to form amides. However, the preparation method involves heating or a high concentration of amines due to the lower reactivity of esters.


Amides Carboxylic Acids Amines Dehydrating Agents Dicyclohexylcarbodiimide (DCC) Synthesis Protonation Acylating Agent Nucleophile Tetrahedral Intermediate Dicyclohexylurea Amide Yield Acid Halides Acid Anhydrides Aminolysis Esters Reactivity

Get cutting-edge science videos from JoVE sent straight to your inbox every month.

Waiting X
Simple Hit Counter