2-(Chloromethyl)-1H-imidazole hydrochloride → 2-[(Imidazole-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazole

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Reaction Steps

1.0 g of 1H-Naphth[2,3-d]imidazole-2-thiol and 0.8 g of 2-chloromethylimidazole-hydrochloride were heated for 11/2 hours at 90° in 20 ml of dimethylformamide. The precipitate formed was filtered off, washed with a small amount of acetonitrile, and dissolved in 2 N sodium bicarbonate solution. The aqueous phase was extracted three times with 30 ml of ethyl acetate. The organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate, and then concentrated by evaporation. The residue was recrystallised from 150 ml of acetonitrile. 150 mg of 2-[(Imidazole-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazole having a melting point of 172° was obtained.

Provenance & Evidence