Potassium Carbonate → HCID 18919027, compound

HRID 1291261Notes

Reaction equation

HRID 1291261 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][C:8]([CH2:13][CH3:14])=[N:7][C:6]=2[N:5]([CH3:15])[C:3]1=[O:4].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:9]3[C:10]4[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:15])[C:6]=4[N:7]=[C:8]3[CH2:13][CH3:14])=[CH:31][CH:30]=2)=[O:28])=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 798388-EthyltheophyllineHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 18919027HCID 18919027, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3-dimethyl-8-ethylxanthine (416 mg) in DMF (10 ml) were added potassium carbonate (332 mg) and 4-(4-chlorobenzoyl)benzyl bromide (619 mg) and the mixture was stirred at room temperature for 21 hours. This 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 distilled off and the residue was recrystallized (ethyl acetate-ether) to provide the title compound as white powder (584 mg, 67%). 1H-NMR (CDCl3) δ: 1.30(3H,t,J=7.6Hz), 2.72(2H,q,J=7.6Hz), 3.40(3H,s), 3.61(3H,s), 5.64(2H,s), 7.21-7.80(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 distilled off
  5. customthe residue was recrystallized (ethyl acetate-ether)

Sources & evidence

ORD record
ord-8898e5f24cf94a9f89c95e07c8338fbc
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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