Benzimidazole → 1-(2-Chloroethyl)-1H-benzimidazole

Participants

Reaction Steps

A mixture of benzimidazole (4.72g, 40 mmol), bromochloroethane (3.4 ml, 41 mmol), potassium carbonate (5.52 g, 40 mmol) and dimethylformamide (60 ml) was stirred at room temperature for 20 hours. To the reaction mixture were added ethyl acetate and water, which was extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous sodium chloride solution, followed by drying (anhydrous sodium sulfate). The solvent was distilled off, and the residue was subjected to a silica gel chromatography (3.0×40 cm: ethyl acetate-hexane=2:1) to give 1-(2-chloroethyl)benzimidazole (5.56 g, 38%) as a colorless oily substance.

Provenance & Evidence