Triethylamine → 1H-Imidazole-2-carbonitrile, 1-(phenylmethyl)-

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In a 50 ml 4-neck flask with stirring bar, nitrogen bubbler, gas inlet tube, thermometer, septum and acetonitrile (20 ml) was bubbled cyanogen chloride (3.1 g, 50 mmol) (ice bath was used to avoid mild heat of solution). The reaction was cooled in an ice bath and a solution of 1-benzylimidazole (3.16 g, 20 mmol) in acetonitrile (ca. 5 ml) was added via syringe. The colorless solution turned yellow-orange and within a few minutes a yellow-orange crystalline solid started to form. After 1 hour, the thick slurry was cooled to -20° C. and triethylamine (7 ml, 50 mmol) was added at such a rate to prevent the temperature from rising above 0° C. The mixture was stirred 1 hour while warming to room temperature, poured into saturated aq NaHCO3 (100 ml) and extracted with ether (3×75 ml). The combined organic layers were dried (MgSO4), evaporated and purified by Kugelrohr distillation. After a forerun of diethylcyanamide, the desired product was collected at 130° C. (0.4 mm) (3.05 g, 83%) as a colorless liquid which crystallized on standing, mp 51°-52° C. (cyclohexane).

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