Amines react with acyl chlorides to give amides
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص202-203
2025-05-10
684
Using the principles we’ve outlined above, you should be able to see how these compounds can be interconverted by substitution reactions with appropriate nucleophiles. We’ve seen that acid chlorides react with carboxylic acids to give acid anhydrides, and with alcohols
to give esters. They also react with amines (such as ammonia) to give amides.
The mechanism is very similar to the mechanism of ester formation. Notice the second molecule of ammonia, which removes a proton, and the loss of chloride ion—the leaving group—to form the amide. Ammonium chloride is formed as a by-product in the reaction.
Here is another example, using a secondary amine, dimethylamine. Try writing down the mechanism now without looking at the one above. Again, two equivalents of dimethyl amine are necessary, although the chemists who published this reaction added three for good measure.
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