N-bromobutanimide → 5-Amino-1-benzyl-2-bromo-1H-imidazole-4-carbonitrile

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Reaction Steps

N-bromosuccinimide (3.55 g, 19.9 mmol) was added portionwise to a suspension of 5-amino-1-benzyl-1H-imidazole-4-carbonitrile (3.59 g, 18.1 mmol) in tetrahydrofuran (50 ml) and the reaction mixture stirred at room temperature for 10 minutes. The solvent was evaporated in vacuo and the residue extracted from a saturated aqueous solution of sodium hydrogen carbonate (50 ml) into ethyl acetate (300 ml), dried over magnesium sulphate, filtered and evaporated in vacuo. The crude material was purified by column chromatography over silica gel eluting with 2-3% dichloromethane:methanol. The material was recrystalised from ethyl acetate, then triturated with diethyl ether to yield the title compound as a pink solid (2.7 g, 9.7 mmol, 53%).

Provenance & Evidence