Hydrochloric Acid → (E)-2-(3-Methylstyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

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Reaction Steps

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-methylcinnamoyl chloride (Amino, Y.; Kawada, K.; Toi, K.; Kumashiro, I.; Fukushima, K. Chem. Pharm. Bull., 1988, 36, 4426) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from 2-propanol/isopropyl ether yielded the titled compound. MW: 347.85; mp: 213.0-235.0° C.; 1H-NMR (DMSO) δ: 8.87-8.82 (1H, m), 8.33-8.20 (2H, m), 7.89 (2H, d, J=8.1 Hz), 7.81-7.74 (1H, m), 7.63-7.45 (5H, m), 7.40-7.24 (2H, m), 7.19 (1H, d, J=16.5 Hz), 2.35 (3H, s).

Provenance & Evidence