Sodium Methoxide → 7-[4-(4-Chlorobenzoyl)benzyl]-1,3-dimethyl-8-methoxyxanthine

HRID 1291254Notes

Reaction equation

HRID 1291254 reaction equation
Cl[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:26])[C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:27])[N:7]([CH3:28])[C:6](=[O:29])[N:5]([CH3:30])[C:4]=2[N:3]=1.[CH3:31][O-:32].[Na+]>CN(C=O)C.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][N:10]3[C:9]4[C:8](=[O:27])[N:7]([CH3:28])[C:6](=[O:29])[N:5]([CH3:30])[C:4]=4[N:3]=[C:2]3[O:32][CH3:31])=[CH:17][CH:16]=2)=[O:26])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 189190388-Chloro-7-[4-(4-chlorobenzoyl)benzyl]-1,3-dimethylxanthine

Product 1

HCID 189189407-[4-(4-Chlorobenzoyl)benzyl]-1,3-dimethyl-8-methoxyxanthineYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-7-[4-(4-chlorobenzoyl)-benzyl]-1,3-dimethylxanthine (866 mg) in DMF (40 ml) was added sodium methoxide (10 ml, 28% in methanol) and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was diluted with water and extracted with ethyl acetate, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was washed with ether to provide the title compound as colorless powder (470 mg, 54%). 1H-NMR (CDCl3) δ: 3.40(3H,s), 3.54(3H,s), 4.17(3H,s), 5.36(2H,s), 7.38-7.78(8H,m).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed 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 ether

Sources & evidence

ORD record
ord-e2a0081dc2ed483184303fd07ee56bad
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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