Ammonia → 1-(4-Amino-3-cyano-5-methylphenyl)-1,2,4-triazole

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Reaction Steps

A mixture of 1-(4-amino-3-iodo-5-methyl-phenyl)-1,2,4-triazole (14.23 g) and cuprous cyanide (5.94 g) was heated at 120° in N-methylpyrrolidone (32 cm3) for 2.5 hours. The cooled mixture was poured into ammonia solution (100 cm3 ; S.G. 0.880) and the resulting solution was extracted with chloroform:methanol, 19:1 (3×150 cm3). The combined and dried (MgSO4) organic extracts were filtered and evaporated in vacuo (0.5 mm) to afford an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:methanol, 19:1. Combination and evaporation of appropriate fractions gave an oil which crystallised on trituration with ether to give the title compound, m.p. 231°-3° (2.8 g).

Provenance & Evidence