Benzyl Chloride → HCID 797337, compound

HRID 495227

Reaction equation

HRID 495227 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=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:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 11430Potassium CarbonateHCID 708212-(2'-Pyridyl)benzimidazole

Product 1

HCID 797337HCID 797337, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2.0 g 2-(2-pyridyl)benzimidazole, 1.8 g potassium carbonate, 30 ml N,N-dimethylformamide and the mixture was stirred under nitrogen at 10 C. 1.5 g benzyl chloride were added and the mixture allowed to warm to 22 C and stirred for 3 hours. Another 0.3 g benzyl chloride was added and the reaction was stirred at 22 C for another 16 hours. The reaction was quenched with 40 ml water and the product was filtered and washed with water. The product was dissolved in 10 ml ethanol and 15 ml of water were added. After cooling to 5 C, the product was filtered, washed and dried resulting in 2.4 g of off-white solid.

Workup

  1. temperatureto warm to 22 C
  2. stirringstirred for 3 hours
  3. stirringthe reaction was stirred at 22 C for another 16 hours
  4. customThe reaction was quenched with 40 ml water
  5. filtrationthe product was filtered
  6. washwashed with water
  7. dissolutionThe product was dissolved in 10 ml ethanol
  8. addition15 ml of water were added
  9. temperatureAfter cooling to 5 C
  10. filtrationthe product was filtered
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-3751bd05e4e54c2ca367a7c2759c8da8
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Linked notes

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