Chlorosuccinimide → 4-Chloro-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

2,2′-Azobisisobutyronitrile (AIBN) (94 mg, 0.57 mmol) was added to a mixture of 7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (2.90 g, 13.3 mmol) and N-chlorosuccinimide (1.95 g, 14.6 mmol) in carbon tetrachloride (250 mL). The mixture was stirred at 70° C. for 2 days. The reaction was concentrated in vacuo, extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to give residue. The residue was crystallized from ethanol/iso-propanol to afford the title compound as colorless crystals (2.28 g, 68%). mp 165-166° C.

Provenance & Evidence