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A Rapid and Efficient Method for Dehydration of Primary Amides to Nitriles. Preparation of Acrylonitrile Derivatives
Authors:T M Bargar  C M Riley
Institution:1. The Procter &2. Gamble Co., Miami Valley Laboratories , Cincinnati, Ohio, 45247
Abstract:Chloromethylene iminium salts (Vilsmeier reagents) have a long history and thoroughly investigated chemistry(1). Chloro-N, N-dimethylforminium chloride 1 is most conveniently generated by the reaction of N, N-dimethylformamide (DMF) with oxalyl chloride(2). The reagent has also been obtained using /></span>thicnyl chloride at elevated temperature and a variety of acid chlorides<sup>(1b)</sup>. The literature describes several examples of the use of thionyl chloride in combination with DMF in which <u class=1 or a related species is thought to function as the reactive intermediate in the transformation of amides to nitriles(3).
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