Potassium Carbonate → HCID 18918859, compound

HRID 1291356Notes

Reaction equation

HRID 1291356 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([CH3:14])=[N:8][C:7]=2[N:6]([CH3:15])[C:4]1=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1>CN(C=O)C.O>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33][N:10]3[C:11]4[C:12](=[O:13])[N:3]([CH2:1][CH3:2])[C:4](=[O:5])[N:6]([CH3:15])[C:7]=4[N:8]=[C:9]3[CH3:14])=[CH:31][CH:30]=2)=[O:28])=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 18919221HCID 18919221, compound

Product 1

HCID 18918859HCID 18918859, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of l-ethyl-3,8-dimethylxanthine (170 mg), a synthetic process for which is described in Journal of American Chemical Society , 75, 114 (1953), in DMF (8 ml) were added potassium carbonate (169 mg) and 4-(4-chlorobenzoyl)benzyl bromide (278 mg) and the mixture was stirred at room temperature for 20 hours. This reaction mixture was diluted with water and extracted with ethyl acetate, and the extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was recrystallized (ethyl acetate-hexane) to provide the title compound as colorless powder (87 mg, 24%).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off
  5. customthe residue was recrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-fbec62f9fd404c9db1e8127a2b9c1deb
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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