Reaktion #64183

Reaktionsgleichung

imidazole

hydrogen

4-(bromomethyl)benzonitrile

sodium hydride

→

4-[1-(imidazolyl)methyl]benzonitrile

Ausbeute 71.9%

Lösungsmittel

N,N-dimethylformamide

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder cooling
2. 2
   workup.STIRRINGthe mixture is agitated for 0.25 hour
3. 3
   Waschenwashed neutral with water
4. 4
   Waschenwashed twice with sodium chloride and water
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated to dryness under vacuum
7. 7
   Sonstigecrystallized from acetone/diethyl ether

Vorschrift

Under cooling, 23.15 g of imidazole in 250 ml of N,N-dimethylformamide is combined in portions with 14.8 g of sodium hydride, 60% in oil, and stirred for 1.5 hours at 25° up to the end of hydrogen release. In two portions, 50 g of 4-(bromomethyl)benzonitrile is added under ice cooling to this solution and the mixture is agitated for 1.5 hours at 25° . For processing, 100 ml of water is added under ice cooling, the mixture is agitated for 0.25 hour, poured into 1.5 1 of ethyl acetate, washed neutral with water, washed twice with sodium chloride and water, dried over sodium sulfate, concentrated to dryness under vacuum, and crystallized from acetone/diethyl ether, thus obtaining 33.6 g of 4-[1-(imidazolyl)methyl]benzonitrile as colorless crystals, mp 102°.

Quelle