Hydrochloric Acid → (E)-2-(3-Methyl-1-butenyl)-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 4-methyl-2-pentenoyl chloride (Yamada, T.; Takashima, K.; Miyazawa, T.; Kuwata, S.; Watanabe, H. Bull. Chem. Soc. Jpn. 1978, 51, 878) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate-hexane to give the titled compound. MW: 299.81; mp: 140.0-141.0° C.; 1H-NMR (DMSO) δ: 8.81-8.79 (1H, m), 8.25 (1H, td, J=8.1, 1.8 Hz), 7.85-7.79 (2H, m), 7.77-7.71 (1H, m), 7.56-7.45 (3H, m), 7.31 (1H, dd, J=16.1, 7.0 Hz), 6.47-6.40 (1H, m), 2.75-2.55 (1H, m), 1.05 (6H, d, J=7.0 Hz).

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