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Master Organic Chemistry Reaction Guide

Formation of amides from acid chlorides and amines

Description: Addition of primary or secondary amines (or ammonia) to acid chlorides results in amides.

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Real-Life Examples:

Org. Synth. 1929, 9, 16

DOI Link: 10.15227/orgsyn.009.0016

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Org. Synth. 1939, 19, 4

DOI Link: 10.15227/orgsyn.019.0004

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Org. Synth. 1941, 21, 4

DOI Link: 10.15227/orgsyn.021.0004

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Org. Synth. 1945, 25, 58

DOI Link: 10.15227/orgsyn.025.0058

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Org. Synth. 1959, 39, 19

DOI Link: 10.15227/orgsyn.039.0019

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Org. Synth. 1945, 25, 71

DOI Link: 10.15227/orgsyn.025.0071

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Org. Synth. 1945, 25, 78

DOI Link: 10.15227/orgsyn.025.0078

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Comments

Comment section

10 thoughts on “Formation of amides from acid chlorides and amines

  1. what product would be derived when acid chloride react with triethylamine with tetrahydrofuran as solvent

    1. For an amino acid like leucine or alanine with non-reactive sidechains, I think you’d need to di-protect the amine as a phthalimide or similar reagent, and then convert it into an acid chloride with SOCl2 or oxalyl chloride. you have to be careful, however – racemization is very facile.

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