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

HRID 501441
Notes
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Reaction equation

HRID 501441 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.CN(C)C=O.[CH2:20]([N:23]1[C:31]2[CH:30]=[CH:29][N:28]=[C:27]([Cl:32])[C:26]=2[NH:25][C:24]1=[O:33])[CH:21]=[CH2:22]>C(OCC)(=O)C.O>[CH2:20]([N:23]1[C:31]2[CH:30]=[CH:29][N:28]=[C:27]([Cl:32])[C:26]=2[N:25]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:24]1=[O:33])[CH:21]=[CH2:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 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 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

0.76 g of potassium carbonate and 0.94 g of benzyl bromide were added to a 50 ml N,N-dimethylformamide solution of 1.05 g of 1-allyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one, and the mixture was stirred at room temperature for 14 hours. 300 ml of water and 300 ml of ethyl acetate were added to the solution, and the organic layer was washed three times with 100 ml of water and then with 100 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to give 1.57 g of the title compound.

Workup

  1. washthe organic layer was washed three times with 100 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b173aea5a05a45b28bf6b2dd5d0453f7
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772226B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes