Potassium Carbonate → HCID 18918837, compound

HRID 1291260Notes

Reaction equation

HRID 1291260 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][C:8]([CH3:13])=[N:7][C:6]=2[N:5]([CH3:14])[C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>CN(C=O)C.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][N:9]3[C:10]4[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:14])[C:6]=4[N:7]=[C:8]3[CH3:13])=[CH:30][CH:29]=2)=[O:27])=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 950308-MethyltheophyllineHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 18918837HCID 18918837, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3,8-trimethylxanthine (0.97 g) in DMF (20 ml) were added potassium carbonate (0.83 g) and 4-(4-chlorobenzoyl)benzyl bromide (1.55 g) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. 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 washed with acetone to provide the title compound as white powder (1.34 g, 61%). 1H-NMR (CDCl3) δ: 2.46(3H,s), 3.41(3H,s), 3.60(3H,s), 5.63(2H,s), 7.25-7.80(8H,m).

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. washthe residue was washed with acetone

Sources & evidence

ORD record
ord-5cca758c25f840afaff349ed16932bc5
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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