Water → 1-Allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

HRID 2112912Notes

Reaction equation

HRID 2112912 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[C:22]([Cl:27])[C:21]=2[NH:20][C:19]1=[O:28])[CH:16]=[CH2:17].O>CN(C)C=O.C(OCC)(=O)C>[CH2:15]([N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[C:22]([Cl:27])[C:21]=2[N:20]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:19]1=[O:28])[CH:16]=[CH2:17]

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 230708521-Allyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

Product 1

HCID 230705921-Allyl-3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-oneYield 104.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.76 g) and benzylbromide (0.94 g) were added to a solution of 1-allyl-4-chloro-1,3-dihydroimidazo[4.5-c]pyridin-2-one (1.05 g) in N,N-dimethylformamide (50 mL). This was stirred at room temperature for 14 hours. Water (300 mL) and ethyl acetate (300 mL) were added, and the organic layer was washed three times with 100 mL of water and then once with 100 mL of saturated aqueous sodium chloride solution, then was dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (1.57 g).

Workup

  1. washthe organic layer was washed three times with 100 mL of water
  2. dry with materialonce with 100 mL of saturated aqueous sodium chloride solution, then was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99e6a1930c43414c81d03b248ca06b0c
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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