Water → 1-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1637655

Reaktionsgleichung

Reaktionsgleichung von HRID 1637655
[NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].Br[CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH3:20].[H-].[Na+].O>CS(C)=O>[CH2:20]([N:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3])[CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 2873381-Bromo-1-hexene

Produkt 1

HCID 128776801-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dioneAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Theobromine (11.9 g, 66 mmol, available from Sigma) was added to a mixture of bromohexene (10.7 g, 66 mmol, available from Aldrich) and sodium hydride (1.58 g, 66 mmol) in dimethylsulfoxide (100 ml) and the resulting mixture stirred for 43 hours. The solution was treated with water (200 ml) and then extracted with three 80 ml aliquots of dichloromethane. The combined extracts were washed with three 100 ml aliquots of water and dried over magnesium sulfate. The solvent was evaporated under vacuum, leaving 17 g of a white powder, 1-(5-hexenyl)-3,7-dimethylxanthine (65 mmol, 98% yield).

Aufarbeitung

  1. extractionextracted with three 80 ml aliquots of dichloromethane
  2. washThe combined extracts were washed with three 100 ml aliquots of water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6ca22e5eeaa245c5a17a7e8178dda198
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043250

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