8-Chlorotheophylline → 8-Chloro-7-[4-(4-chlorobenzoyl)benzyl]-1,3-dimethylxanthine

HRID 1291253Notes

Reaction equation

HRID 1291253 reaction equation
[Cl:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.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:1][C:2]1[N:11]([CH2:32][C:31]2[CH:30]=[CH:29][C:28]([C:26](=[O:27])[C:25]3[CH:36]=[CH:37][C:22]([Cl:21])=[CH:23][CH:24]=3)=[CH:35][CH:34]=2)[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 106618-ChlorotheophyllineHCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 189190388-Chloro-7-[4-(4-chlorobenzoyl)benzyl]-1,3-dimethylxanthineYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chlorotheophylline (2.15 g) in DMF (20 ml) was added potassium carbonate (1.66 g) as well as 4-(4-chlorobenzoyl)benzyl bromide (3.10 g) and the mixture was stirred at room temperature for 20 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 then distilled off and the residue was washed with ether to provide the title compound as white powder (3.34 g, 75%). 1H-NMR (CDCl3) 6: 3.41(3H,s), 3.57(3H,s), 5.64(2H,s), 7.41-7.52(4H,m), 7.68-7.80(4H,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 ether

Sources & evidence

ORD record
ord-8e792f3ac9674844898138fa6639107f
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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