Abstract
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 O-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.
GRAPHICAL ABSTRACT
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ACKNOWLEDGMENT
The authors thank James A. Ciaccio for obtaining the GC-MS data and making helpful comments on the manuscript.
SUPPLEMENTAL MATERIAL
Full experimental details and IR, 1H NMR, and HRMS data for this article can be accessed on the publisher’s website.