Réaction #79160

Équation de réaction

hydrogen chloride

N-(2-pyridyl)-o-phenylenediamine

(E)-2-methylcinnamoyl chloride

(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

→

titled compound

(E)-2-(2-Methylstyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   ConcentrationConcentration and recrystallization from ethyl acetate/ethanol

Mode opératoire

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-2-methylcinnamoyl chloride (Sekiya, T.; Hiranuma, H.; Hata, S.; Mizogami, S.; Hanazuka, M.; Yamada, S. J. Med. Chem., 1983, 26, 411) 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: 347.85; mp: 212.0-215.0° C.; 1H-NMR (CDCl3) δ: 9.26 (1H, d, J=16.1 Hz), 8.89-8.83 (1H, m), 8.24-8.12 (2H, m), 7.72-7.64 (2H, m), 7.59-7.43 (4H, m), 7.43-7.11 (3H, m), 6.92 (1H, d, J=16.1 Hz), 2.70 (3H, s).

Source