Water → 3-Methyl-7-[4-(4-chlorobenzoyl)benzyl]xanthine

HRID 1291251

Reaktionsgleichung

Reaktionsgleichung von HRID 1291251
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1.O>CN(C=O)C.C(OCC)(=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30][N:7]3[C:6]4[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=4[N:9]=[CH:8]3)=[CH:28][CH:27]=2)=[O:25])=[CH:34][CH:35]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 706393-MethylxanthineHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Produkt 1

HCID 189188013-Methyl-7-[4-(4-chlorobenzoyl)benzyl]xanthineAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-methylxanthine (1.06 g) in DMF (26 ml) were added potassium carbonate (1.06 g) and 4-(4-chlorobenzoyl)benzyl bromide (1.98 g) and the mixture was stirred at room temperature for 24 hours. To this reaction mixture were added water and ethyl acetate and the floating matter was filtered off and the filtrate aqueous solution was diluted with 1N-hydrochloric acid and extracted with chloroform. 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 ethyl acetate to provide the title compound as colorless powder (239 mg, 10%). 1H-NMR (CDC13) 8: 3.54(3H,s), 3.57(3H,s), 7.41-7.52(4H,m), 7.68-7.81(5H,m).

Aufarbeitung

  1. filtrationthe floating matter was filtered off
  2. additionthe filtrate aqueous solution was diluted with 1N-hydrochloric acid
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off
  7. washthe residue was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-263f4060c9a346398982594f4c89d517
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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