Theophylline → HCID 18919192, compound

HRID 1291249Notes

Reaction equation

HRID 1291249 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>CN(C=O)C.O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31][N:10]3[C:11]4[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=4[N:8]=[CH:9]3)=[CH:29][CH:28]=2)=[O:26])=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 18919192HCID 18919192, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of theophylline (1.80 g) in DMF (20 ml) were added potassium carbonate (1.66 g) and 4-(4-chlorobenzoyl)benzyl bromide (3.10 g) and the mixture was stirred at room temperature for 14 hours. The reaction mixture was then 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 purified by silica gel column chromatography (hexane: ethyl acetate=1:4) to provide the title compound as colorless powder (2.79 g, 68%). 1 H-NMR (CDCl3) 6: 3.41(3H,s), 3.63(3H,s), 5.59(2H,s), 7.38-7.50(4H,m), 7.65(1H,s), 7.68-7.81(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. customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:4)

Sources & evidence

ORD record
ord-5a4a4dc3dd6946618df3d80e442892d1
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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