Benzimidazole → HCID 799461, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 1.86 g, 46.6 mmol) in dry DMF (5 mL) under nitrogen and cooled to 0° C. was added a solution of benzimidazole (5.0 g, 42.2 mmol) in DMF (15 mL) and the reaction mixture was allowed to stir for 30 min at room temperature. The reaction mixture was cooled to 0° C. and a solution of 4-bromobenzyl bromide (10.6 g, 42.4 mmol) in DMF (10 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature overnight. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (Na2SO4) and evaporated. The crude product was triturated with ethyl ether and recovered by filtration. Yield: 70%. LCMS (ESI+) 387.2 and 389.2 (MH+).

Provenance & Evidence