Tetrahydrofuran → HCID 53927404, compound

Participants

Reaction Steps

Three hundred milligrams (1.08 mmoles) of 1-isopropyl-2-amino-6-(1-phenylethenyl)benzimidazole and 192 mg. (1.08 mmoles) of N-bromosuccinimide were refluxed overnight in 20 ml. of dry tetrahydrofuran. After cooling, ethyl acetate was added and the solution was washed with a saturated solution of sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue was chromatographed over silica gel, first eluting with ethyl acetate to remove impurities, and then with 10% methanol/90% ethyl acetate. The title product was crystallized from ether giving 200 mg. of the cis/trans mixture, M+ =357.

Provenance & Evidence