Benzyl Chloride → 1-Benzyl-2-phenyl-1H-benzoimidazole

HRID 495226Notes

Reaction equation

HRID 495226 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 128552-Phenylbenzimidazole

Product 1

HCID 12216871-Benzyl-2-phenyl-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 3 g 2-phenylbenzimidazole, 2.8 g potassium carbonate, 40 ml N,N-dimethylformamide and the mixture was stirred under nitrogen. 3.6 g Benzyl chloride were added and the mixture was heated to 75 C for 8 hrs. The reaction was cooled to 50 C and quenched with 40 ml of water and cooled to 5 C. The product was filtered, washed with water. The product was recrystallized by dissolving in 57 ml acetonitrile at reflux and 39 ml water were added. After cooling to 5 C, the product was filtered, washed and dried giving 3.1 g.

Workup

  1. temperaturethe mixture was heated to 75 C for 8 hrs
  2. temperatureThe reaction was cooled to 50 C
  3. customquenched with 40 ml of water
  4. temperaturecooled to 5 C
  5. filtrationThe product was filtered
  6. washwashed with water
  7. customThe product was recrystallized
  8. dissolutionby dissolving in 57 ml acetonitrile
  9. temperatureat reflux
  10. addition39 ml water were added
  11. temperatureAfter cooling to 5 C
  12. filtrationthe product was filtered
  13. washwashed
  14. customdried
  15. customgiving 3.1 g

Sources & evidence

ORD record
ord-d2d72b1f2cc14ea2a3db845bbaff336f
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Reaction notes

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