Benzimidazole → 4-(1H-Benzimidazol-1-yl)butanenitrile

Reaktionsgleichung

[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Cl[CH2:13][CH2:14][CH2:15][C:16]#[N:17]>O1CCOCC1>[N:1]1([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

Versuchsvorschrift

To a suspension of 23.6 grams of benzimidazole in 300 ml of dioxane is added 9.8 grams of a 50% dispersion of sodium hydride in mineral oil and the resulting mixture is stirred at room temperature for two hours. Then a solution of 20.7 grams of 4-chlorobutyronitrile in 100 ml of dioxane is added and the mixture is refluxed for 5 hours. An additional 3 grams of sodium hydride suspension is added and the mixture refluxed for 17 hours. The mixture is then filtered, concentrated, and washed with petroleum ether to remove the mineral oil. The residual oil is then chromatographed on silica gel packed with chloroform and eluted with chloroform and chloroform containing increasing quantities of methanol. The fractions eluted with 0.5% and 1% methanol are combined and the solvent is evaporated to obtain 1H-benzimidazole-1-butanenitrile.