1-(4-(4H-1,2,4-triazol-4-yl)phenyl)hydrazine dihydrochloride → HCID 22009915, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-(1,2,4-triazol-4-yl)phenylhydrazine hydrochloride (930 mg, 3.5 mmol) in ethanol/water (25 ml, 4:1), under nitrogen, was slowly treated with a solution of 4-[4-(tert-butyldimethylsilanyloxy)cyclohexyl]butyraldehyde (1 g, 3.5 mmol) in ethanol (5 ml). The reaction mixture was heated at 140° C. for 18 hours in a sealed tube, cooled and evaporated. The residue was purified by column chromatography on silica using methanol/dichloromethane as eluent to afford the title compound as a mixture of cis and trans isomers (1 g, 92%). MS, ES+, m/z=311 for (M+H)+, δ(250 MHz, d6-DMSO) 1.07-1.88 (11H, m), 2.71 (2H, t, J=7 Hz), 3.70-3.78 (1H, m), 4.26 (1H, d, J=3 Hz), 7.21-7.32 (2H, m), 7.47 (1H, d, J=9Hz), 7.76 (1H, d, J=2Hz), 9.02 (2H, s), 11.10 (1H, br s).

Provenance & Evidence