Benzyl Chloride → 1-Benzyl-4-methyl-1H-benzimidazole

HRID 495230

Reaction equation

HRID 495230 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 11430Potassium CarbonateHCID 15193414-Methylbenzimidazole

Product 1

HCID 149330241-Benzyl-4-methyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 1.0 g 4-methyl-1H-benzimidazole, 1.6 g potassium carbonate, 25 ml N,N-dimethylformamide and the mixture was stirred under nitrogen. 1.4 g Benzyl chloride were added and the mixture was heated to 60 C for 16 hours. Another 0.4 g of benzyl chloride were added and the reaction was heated to 70 C for 24 hours. The reaction was cooled to 50 C and quenched with 50 ml water and extracted with ethyl acetate. After washing with water, the solvent was removed and the product was purified by column chromatography using a gradient from 40% ethyl acetate in hexane to 75% ethyl acetate in hexane. Following removal of the solvent, the partially crystallized product was dissolved in 20 ml acetonitrile and treated with 0.1 g activated carbon. After refluxing for 20 minutes, the mixture was filtered through celite and the solvent was removed leaving a yellow oil which crystallized on standing, 1.0 g.

Workup

  1. temperaturethe mixture was heated to 60 C for 16 hours
  2. temperaturethe reaction was heated to 70 C for 24 hours
  3. temperatureThe reaction was cooled to 50 C
  4. customquenched with 50 ml water
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. customthe solvent was removed
  8. customthe product was purified by column chromatography
  9. customremoval of the solvent
  10. dissolutionthe partially crystallized product was dissolved in 20 ml acetonitrile
  11. additiontreated with 0.1 g
  12. temperatureAfter refluxing for 20 minutes
  13. filtrationthe mixture was filtered through celite
  14. customthe solvent was removed
  15. customleaving a yellow oil which
  16. customcrystallized

Sources & evidence

ORD record
ord-218b782235a04ad585e99327bd7560fa
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Linked notes

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