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Synthesis 2018; 50(10): 2041-2057
DOI: 10.1055/s-0037-1609342
DOI: 10.1055/s-0037-1609342
paper
Latent Brønsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides
This work was supported financially by the University of Tokyo. All authors acknowledge this support.Further Information
Publication History
Received: 19 January 2018
Accepted after revision: 20 February 2018
Publication Date:
20 March 2018 (online)

Abstract
Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N,N-dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Brønsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609342.
- Supporting Information
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