Novel Syntheses of Heterocycles with N‐(1‐Haloalkyl)Azinium Halides Part 1. Preparation of Imidazolidines

Abstract

N-(1-Chloroalky1)pyridinium chlorides, prepared from thionyl chloride, pyridine, and an aldehyde, readily react with N,N'-disubstituted 1,2-ethanediamine to yield imidazolidines under mild and neutral conditions. N-[Chloro(2-chlorophenyl)methyl]pyridinium chloride (lc; not isolated) nmr (CH,Cl,poorly soluble): 9.7 (d, 2H, H2 and Hb pyr); 9.1-8.4 (c, 7H) ppm.N-[Chloro(4-methoxyphenyl)methyl]pyridinium chloride (la; not isolated) nmr (CH,Cl,): 9.8 (d, 2H, H2 and Hs pyr); 8.9 ( s , lH, CHC1); 8.6 (t, lH, H ' pyr); 8.2 (t, 2H, H3 and H5 pyr); 7.7 (d, 2H, H2 and H6 ph); 6.9 (d, 2H, H3 and H5 ph); 3.7 ( s , 3H, OCH,) ppm.