Methanol → 5-(4-methoxybenzyl)-1H-1,2,4-triazol-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of N-aminoguanidine nitrate (5.50 g, 40 mmol) and anhydrous methanol (50 mL) cooled to 0 C was added sodium methoxide solution (25% in methanol, 9.2 mL, 40 mmol) dropwise. The resulting mixture was stirred at 0° C. for 10 min before methyl 2-(4-methoxyphenyl)acetate (1.6 mL, 10 mmol) was added. The mixture was then stirred at 0° C. for 10 min, RT for 10 min, and 75° C. for 27 hr. The reaction mixture was cooled and diluted with 20 mL of water. Methanol was removed under vacuum and the aqueous solution was acidified to pH=3-4 with 3 N aqueous HCl solution. The solid obtained was filtered, washed with water, and recrystalized in ethanol-water to give 1.65 g (81% yield) of 5-(4-methoxybenzyl)-1H-1,2,4-triazol-3-amine as a white solid. (M+H)+=205.22

Provenance & Evidence