Theophylline → 7-[4-(2,4-Dichlorobenzoyl)benzyl]-1,3-dimethyl-xanthine

HRID 1291257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291257
[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]=[C:35]([Cl:37])[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]=[C:35]([Cl:37])[CH:34]=[CH:33][C:22]=1[C:23]([C:25]1[CH:26]=[CH:27][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:31][CH:32]=1)=[O:24]

Komponenten

6

Edukt 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 189192794-(2,4-Dichlorobenzoyl)benzyl bromide

Produkt 1

HCID 189191327-[4-(2,4-Dichlorobenzoyl)benzyl]-1,3-dimethyl-xanthineAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of theophylline (1.80 g) in DMF (20 ml) were added potassium carbonate (1.66 g) and 4-(2,4-dichlorobenzoyl)benzyl bromide (3.33 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 then distilled off and the residue was recrystallized (ethyl acetate) to provide the title compound as white powder (3.38 g, 76%). 1H-NMR (CDCl3) δ: 3.39(3H,s), 3.60(3H,s), 5.58(2H,s), 7.25-7.84(8H,m).

Aufarbeitung

  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 recrystallized (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cb672e19e8224ff0bd697630544e30a0
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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