Hydrochloric Acid → 2-Hydroxy benzimidazole

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Reaction Steps

Following the procedure of Harrison et al., J.Chem.Soc., 1963, 2930-2937, 15 g benzimidazolin-2-one is boiled under reflux for 31/2 hours with 150 ml phosphoryl chloride, dry hydrogen chloride being passed through the refluxing mixture for the last three hours of the reaction. The excess phosphoryl chloride is removed at about 40 mm and the residue treated with about 40 ml of ice water. The cold acid solution is filtered, and the insoluble unreacted benzimidolin-2-one is washed with dilute hydrochloric acid, then with water. The filtrate and washings are made just alkaline, as determined by a litamus test, by the addition of dilute ammonia solution. After thorough cooling, crude 2-chlorobenzimidazole is collected, washed with water and dried. The reaction sequence yields 0.5 g of unreacted benzimidazolin-2-one and 15.6 g of title compound which has a m.p. of 180° C. (softens, bubbles, then resolidifies).

Provenance & Evidence