Direct Preparation of Amides from Amine Hydrochloride Salts and Orthoesters: A Synthetic and Mechanistic Perspective
Martin J. Di Grandi
Caitlin Bennett
Kristen Cagino
Arnold Muccini
Corey Suraci
Shahrokh Saba
10.6084/m9.figshare.1568608.v2
https://tandf.figshare.com/articles/journal_contribution/Direct_Preparation_of_Amides_from_Amine_Hydrochloride_Salts_and_Orthoesters_A_Synthetic_and_Mechanistic_Perspective/1568608
<div><p></p><p>The conversion of a wide range of primary and secondary aliphatic and a few arylamine hydrochloride salts to their corresponding acetamides with trimethyl orthoacetate is described. Mechanistic studies using NMR and gas chromatography–mass spectrometry techniques indicate these reactions proceed via an <i>O</i>-methylimidate intermediate that undergoes in situ demethylation by chloride, affording the corresponding acetamides. Synthetically, this reaction represents a practical, high-yielding protocol with a simple workup for the rapid conversion of amine hydrochloride salts to acetamides.</p></div>
2015-11-18 20:43:35
amine hydrochloride salts
Mechanistic Perspective
conversion
arylamine hydrochloride salts
Mechanistic studies
acetamide
nmr
Direct Preparation
trimethyl orthoacetate