Benzyl Chloride → 1-benzyl-2-methylbenzimidazole

HRID 1926469Notes

Reaction equation

HRID 1926469 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

Conditions

Temperature
6 °C

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

Sources & evidence

ORD record
ord-7a73599447064937bbecab6bc329b186
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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