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

Temperature

55 °C

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).

1. temperatureThe reaction mixture was cooled to room temperature
2. temperatureThe reaction mixture was refluxed for 3 hours
3. customAfter the completion of reaction
4. temperaturethe mass was cooled to 25° C.
5. filtrationthe insolubles filtered
6. concentrationThe filtrate was concentrated to residue under vacuum
7. dissolutionThe residue was dissolved in dichloromethane (500 ml)
8. washwashed with saturated solution of sodium chloride
9. concentrationconcentrated under vacuum
10. additionTo the residue, a mixture of diisopropyl ether (160 ml) and n-Heptane (160 ml)
11. additionwas added
12. filtrationfiltered
13. washwashed with n-Heptane
14. customdried under vacuum at 40-45° C.

ORD record

ord-b10ce099d1b84abfbab362ea753b1f80

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003804B2