Potassium Iodide → 4-(1,2,4-Triazol-1-ylmethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

Acetone (1500 ml), 1,2,4-triazole (200 gm; 2.895 mol. eq), cesium carbonate (142 gm; 0.436 mol. eq) and potassium iodide (9 gm) was heated to reflux (55° C.) for 4 hours. The reaction mixture was cooled to room temperature. To this, a solution of 4-bromomethyl benzonitrile (100 gm; 0.510 mol. eq) in dichloromethane (450 ml) was added over a period of 2 hours. The reaction mixture was refluxed for 3 hours. After the completion of reaction, the mass was cooled to 25° C. and the insolubles filtered. The filtrate was concentrated to residue under vacuum. The residue was dissolved in dichloromethane (500 ml), washed with saturated solution of sodium chloride, acidified to a pH 1.0 with concentrated hydrochloric acid and concentrated under vacuum. To the residue, a mixture of diisopropyl ether (160 ml) and n-Heptane (160 ml) was added, stirred at 10° C. for 30 minutes, filtered, washed with n-Heptane and dried under vacuum at 40-45° C. to give 4-[1-(1,2,4-triazole-1-yl)methyl]benzonitrile (76 gm, 81% yield, 99.0% HPLC purity).

Provenance & Evidence