Benzimidazole → 1-Benzyl-1H-benzimidazole

HRID 1926475Notes

Reaction equation

HRID 1926475 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 5633471-Benzyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a flask were added 2 g benzimidazole, 3.5 g potassium carbonate, 20 ml N,N-dimethylformamide and the mixture was stirred under nitrogen. 3.2 g Benzyl chloride were added and the mixture was heated to 5° C. for 16 hrs. The reaction was quenched with 40 ml water and 7 ml 3M hydrochloric acid and cooled to 5 C. The product was filtered and washed with water. The product was recrystallized by dissolving in 10 ml 2-propanol at reflux, hot filtered and 30 ml hexane were added. After cooling to 5 C, the product was filtered, washed with hexane and dried giving 1.6 g.

Workup

  1. customThe reaction was quenched with 40 ml water and 7 ml 3M hydrochloric acid
  2. temperaturecooled to 5 C
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customThe product was recrystallized
  6. dissolutionby dissolving in 10 ml 2-propanol
  7. temperatureat reflux
  8. filtrationhot filtered
  9. addition30 ml hexane were added
  10. temperatureAfter cooling to 5 C
  11. filtrationthe product was filtered
  12. washwashed with hexane
  13. customdried
  14. customgiving 1.6 g

Sources & evidence

ORD record
ord-4bbecd73b685492aa351e726b87f5b92
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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