Reaktion #64190

Reaktionsgleichung

4-(bromomethyl)benzonitrile

sodium hydride

1,2,4-triazole

hydrogen

→

4-[1-(1,2,4-triazolyl)methyl]benzonitrile

Ausbeute 67.5%

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added under ice cooling
2. 2
   workup.STIRRINGthe mixture is stirred for 1 hour
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   Waschenwashed neutral with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated to dryness under vacuum
7. 7
   Sonstigechromatographed on silica gel with dichloromethane/methanol

Vorschrift

23.5 g of 1,2,4-triazole is combined under cooling in 250 ml of N,N-dimethylformamide in incremental portions with 14.15 g of sodium hydride, 60% in oil, and stirred at 25° for 1 hour until hydrogen release has ceased. To this solution is added 50 g of 4-(bromomethyl)benzonitrile in two portions under ice cooling at 5°, and the mixture is stirred for 2 hours at 25°. For working up purposes, 200 ml of water is added under ice cooling, the mixture is stirred for 1 hour, extracted with ethyl acetate, washed neutral with water, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with dichloromethane/methanol, yielding 31.73 g of 4-[1-(1,2,4-triazolyl)methyl]benzonitrile as colorless crystals, mp. 72°-73°.

Quelle