Water → 2-Methyl-1-[4-(3-tolyloxy)benzyl]benzimidazole

HRID 65088

Reaction equation

HRID 65088 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[C:13]1([CH3:28])[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=2)[CH:14]=1.O>CN(C)C=O>[CH3:3][C:4]1[N:8]([CH2:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:15]3[CH:14]=[C:13]([CH3:28])[CH:18]=[CH:17][CH:16]=3)=[CH:27][CH:26]=2)[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 119842-MethylbenzimidazoleHCID 24758Sodium hydrideHCID 135633881-[4-(Bromomethyl)phenoxy]-3-methylbenzene

Product 1

HCID 135633892-Methyl-1-[4-(3-tolyloxy)benzyl]benzimidazoleYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitin 30 minutes
  4. stirringby stirring at room temperature overnight
  5. customAfter completion of the reaction
  6. extractionextracted with toluene (30 ml) two times
  7. washThe toluene layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove toluene
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08a58585747d41ad85499f45bf9e714f
Source dataset
uspto-grants-1986_09
Patent number
US04612323

Linked notes

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