반응 #352543

반응 방정식

water

2,4,5-Triphenylimidazole

sodium hydride

1,8-dibromo-octane

→

1-(8-bromooctyl)-2,4,5-triphenylimidazole

수율 50.0%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   온도cooled
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature for 24 h
3. 3
   기타the solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (500 ml)
5. 5
   세척washed with water (250 ml), 2N aqueous hydrochloric acid (250 ml), saturated sodium chloride solution (250 ml)
6. 6
   건조dried over anhydrous magnesium sulphate
7. 7
   기타evaporated to dryness in vacuo
8. 8
   workup.DISTILLATIONDistillation
9. 9
   기타to remove 1,8-dibromooctane and chromatography on silica gel
10. 10
    세척eluted with dichloromethane

실험 절차

2,4,5-Triphenylimidazole (5 g) was added to a suspension of sodium hydride (1.0 g) (50% dispersion in oil, washed with hexane) in dry dimethylformamide (80 ml) under nitrogen. The reaction was stirred at 45° C. for 1 h, cooled and added, over 1 h to a solution of 1,8-dibromo-octane (30 g) in dry dimethylformamide (100 ml) under nitrogen. The reaction was stirred at room temperature for 24 h, water was carefully added and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (500 ml), washed with water (250 ml), 2N aqueous hydrochloric acid (250 ml), saturated sodium chloride solution (250 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Distillation to remove 1,8-dibromooctane and chromatography on silica gel eluted with dichloromethane gave 1-(8-bromooctyl)-2,4,5-triphenylimidazole (4.1 g, 50%) as an oil; NMR d (CDCl3) 0.9-1.7 (12H, m, 6×CH2), 3.3 (2H, t, BrCH2), 3.9 (2H, t, N--CH2), 7.1-7.7(15H, m, 3×Ph) ppm.

출처