Acrylamidines and Polyacrylamidines. Part 2. A New Synthesis of N‐Substituted Acrylamidines

Abstract

AbstractN‐substituted acrylamidines, a new class of acrylic monomers have been obtained recently(1) from acrylonitrile, an alkyl halide, a Lewis acid and an amine.I would like to report on a new synthesis starting from β‐chloropropionitrile 1 following the general method previously published(2).The N‐alkylation of 1 with isopropyl chloride in the presence of ferric chloride gives N‐isopropyl‐β‐chloropropionitrilium tetrachloroferrat 2. Its aminolysis with aniline provides the amidinium salt 3 whose neutralization furnishes the N‐isopropyl‐N′‐phenyl‐β‐chloropropionamidine 4. This rearranges on standing at room temperature within an hour or two into the hydrochloride of N‐isopropyl‐N′‐phenylacrylamidine 5 identical with the compound prepared from acrylonitrile (1).