Benzyl Chloride → 1-benzyl-2-methylbenzimidazole

HRID 1471216Notes

Reaction equation

HRID 1471216 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=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:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[CH3:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 119842-Methylbenzimidazole

Product 1

HCID 7593051-benzyl-2-methylbenzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2.5 g 2-methylbenzimidazole, 3.9 g potassium carbonate, 60 ml N,N-dimethylformamide and the mixture was stirred under nitrogen. 3.6 g Benzyl chloride were added and the mixture was heated to 60 C for 16 hours. The reaction was quenched with 80 ml water and cooled to 22 C. The product was extracted twice with 50 ml ethyl acetate and washed with water. Following removal of solvent, the product was dissolved in 100 ml hexane and washed with two portions of water. After drying the hexane layer over sodium sulfate, the mixture was filtered and stripped down to an orange oil.

Workup

  1. temperaturethe mixture was heated to 60 C for 16 hours
  2. customThe reaction was quenched with 80 ml water
  3. temperaturecooled to 22 C
  4. extractionThe product was extracted twice with 50 ml ethyl acetate
  5. washwashed with water
  6. customremoval of solvent
  7. dissolutionthe product was dissolved in 100 ml hexane
  8. washwashed with two portions of water
  9. dry with materialAfter drying the hexane layer over sodium sulfate
  10. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-84772fef4ca549128e0b7314a1796bc0
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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