Theophylline → HCID 18919183, compound

HRID 1291259Notes

Reaction equation

HRID 1291259 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][CH:34]=[CH:33][C:22]=1[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)=[O:24]>CN(C=O)C.O>[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[CH:33][C:22]=1[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][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)=[CH:27][CH:26]=1)=[O:24]

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 18919154[4-(Bromomethyl)phenyl](2-chlorophenyl)methanone

Product 1

HCID 18919183HCID 18919183, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of theophylline (0.90 g) in DMF (20 ml) were added potassium carbonate (0.83 g) and 4-(2-chlorobenzoyl)benzyl bromide (1.55 g) and the mixture was stirred at room temperature for 13 hours. This reaction mixture was diluted with water and extracted with ethyl acetate and 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 needles (1.70 g, 83%). 1H-NMR (CDCl3) δ: 3.39(3H,s), 3.60(3H,s), 5.58(2H,s), 7.30-7.48(6H,m), 7.63(1H,s), 7.76-7.85(2H,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-b335274f9a0e42b7b1b7a1b34bb80761
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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