Theophylline → HCID 18919186, compound

HRID 1291256Notes

Reaction equation

HRID 1291256 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:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[CH2:30]Br)=[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:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[CH2:30][N:10]2[C:11]3[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=3[N:8]=[CH:9]2)=[O:26])=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 136496533-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 18919186HCID 18919186, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of theophylline (1.80 g) in DMF (50 ml) were added potassium carbonate (1.66 g) and 3-(4-chlorobenzoyl)benzyl bromide (3.10 g) and the mixture was stirred at room temperature for 24 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 (acetone-hexane) to provide the title compound as white powder (1.64 g, 40%). 1H-NMR (CDCl3) δ: 3.40(3H,s), 3.60(3H,s), 5.57(2H,s), 7.42-7.79(9H,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 (acetone-hexane)

Sources & evidence

ORD record
ord-1bb6e1ba4e3c4b82ae83ca0c26a9868f
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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