4-CYANOIMIDAZOLE

Preparation

A mixture of ethyl 4-imidazolecarboxylate (33 g) and ammonium hydroxide (250 mL) was heated to 100 C° in a sealed glass vessel for 1–7 days. The mixture was then cooled and the solid 4-imidazolecarboxamide 1443 was recovered by filtration in near quantitative yield and air dried. Dehydration was carried out by heating a solution of 4-imidazolecarboxamide 1443 (5 g) in PhPOCl2 (25 mL) at 80 C° for 12 h. The cooled reaction mixture was then poured over ice (200 mL) and adjusted to pH 11 with 50% aqueous sodium hydroxide. The 4-cyanoimidazole 1444 was isolated by extraction with ethyl acetate and concentration of the extracts in vacuo.