Water → (E)-1-(6-Methoxypyridin-2-yl)-2-styryl-1H-benzimidazole hydrochloride

Participants

Reaction Steps

According to the literature procedure (Trecourt, F.; Mallet, M.; Mongin, O.; Queguiner, G. J. Org. Chem. 1994, 59, 6173.), a solution of (E)-1-(6-chloropyridin-2-yl)-2-styryl-1H-benzimidazole (145 mg, 0.44 mmol), 28% NaOEt in MeOH (3 ml) and toluene (5 ml) was maintained at room temperature for 2 h then heated under reflux condition for 1 h. To this solution, water (1 ml) was added and it was concentrated by evaporator. To this residue, water (5 ml) was added and the whole was extracted with CH2Cl2 (2×15 ml). Combined organic layer was dried (magnesium sulfate) and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, 20 g; n-hexane/ethyl acetate (5/1)) to afford the desired compound (35 mg, 24%). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate/n-hexane to give the titled compound.

Provenance & Evidence