1H-1,2,4-Triazole-3-acetonitrile,5-(1-methylethyl)-(9CI) synthesis

Yield:168260-22-8 76%

Reaction Conditions:

with sodium hydroxide in methanol; for 2.5 h;Heating / reflux;

Steps:

80 (5-Isopropyl-4H-[1,2,4]triazol-3-yl)-acetonitrile (I-80)

A methanol (100 ml) solution of 2.04 g (51.0 mmol) of sodium hydroxide was mixed with 6.88 g (50.0 mmol) of methyl isobutylimidate hydrochloride (I-58) and 5.46 g (51.5 mmol) of cyanoacetohydrazide and heated under reflux for 2.5 hours. After cooling, the reaction solution was concentrated under a reduced pressure, the thus obtained residue was applied to a silica gel column chromatography, and 5.85 g (76%) of the title compound was obtained as colorless crystals from an eluate of chloroform-methanol (75:1 v/v). MS (FAB)m/z: 151 (M+1)⁺. ¹H-NMR (CDCl₃)δ: 1.39 (6H, d, J= 6.9 Hz), 3.16 (1H, sep, J= 6.9 Hz), 3.89 (2H, s), 11.04 (1H, brs).

References:

EP1717238,2006,A1 Location in patent:Page/Page column 63