Sodium hydride → HCID 3822419, compound

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Reaction Steps

Benzotriazole (238 mg, 2 mmol) in 4 mL of anhydrous N,N-dimethylformamide was added sodium hydride (60% in mineral oil, 88 mg, 2.2 mmol). After stirring for 1 hour, 2-iodomethyl-1-methanesulfonyl benzimidazole (740 mg, 2.2 mmol) was added. The resulting solution was stirred for 6 hours, diluted with water, and extracted with diethyl ether. The combined extracts were dried over magnesium sulfate, and evaporated. To the residue was added 5 mL of methanol and hydrazine (0.5 mL), and stirred at 65° C. overnight. The solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography (EtOAc: hexane=1:1 to 2:1) to give 24 mg (5%) of 2-(1H-benzimidazol-2-ylmethyl)-2H-benzotriazole (IV), and 240 mg (48%) of 1-(1-benzimidazol-2-ylmethyl)-1H-benzotriazole (III) as solids.

Provenance & Evidence