تفاعل #93366

معادلة التفاعل

sodium hydride

2-methylbenzimidazole

4-(3-tolyloxy)benzyl bromide

water

→

2-methyl-1-[4-(3-tolyloxy)benzyl]benzimidazole

المردود 71.1%

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITin 30 minutes
4. 4
   workup.STIRRINGby stirring at room temperature overnight
5. 5
   أخرىAfter completion of the reaction
6. 6
   استخلاصextracted with toluene (30 ml) two times
7. 7
   غسيلThe toluene layer was washed with water
8. 8
   تجفيفdried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONdistilled under reduced pressure
10. 10
    أخرىto remove toluene
11. 11
    أخرىThe residue was purified by silica gel column chromatography

الإجراء التجريبي

To a suspension of sodium hydride (0.14 g, 3.6 mmole; 62% in oil) in anhydrous dimethylformamide (10 ml), 2-methylbenzimidazole (0.48 g, 3.6 mmole) was added while stirring, and stirring was continued at room temperature for 1 hour. The resultant mixture was cooled to 5°-10° C., and a solution of 4-(3-tolyloxy)benzyl bromide (1.00 g, 3.6 mmole) in anhydrous dimethylformamide (5 ml) was dropwise added thereto in 30 minutes, followed by stirring at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water (100 ml) and extracted with toluene (30 ml) two times. The toluene layer was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 2-methyl-1-[4-(3-tolyloxy)benzyl]benzimidazole (0.84 g) as colorless liquid. nD27.0 1.6112.

المصدر