Hydrochloric Acid → (E)-1-(2-Pyridyl)-2-(4-fluorostyryl)-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)-4-fluorocinnamoyl 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 ethyl acetate/ethanol yielded the titled compound. MW: 351.81; mp:>230° C.; 1H-NMR (CDCl3) δ: 9.10 (1H, d, J=16.5 Hz), 8.89-8.84 (1H, m), 8.24-8.12 (2H, m), 7.72-7.43 (6H, m), 7.07 (2H, dd, J=8.4, 8.4 Hz), 6.91 (1H, d, J=16.5 Hz), 6.82 (1H, dd, J=8.8, 8.8 Hz).

Provenance & Evidence