Carbon Dioxide → 1-(5-Acetoxy-6-bromohexyl)-3,7-dimethylxanthine

HRID 376245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376245
[OH:1][CH:2]([CH2:20]O)[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9].[BrH:22].[C:23]([OH:26])(=O)[CH3:24].C(=O)(O)[O-].[Na+].C(=O)=O>>[C:23]([O:1][CH:2]([CH2:20][Br:22])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9])(=[O:26])[CH3:24]

Komponenten

5

Edukt 4

HCID 280Carbon DioxideHCID 516892Sodium BicarbonateHCID 158959551-(5,6-Dihydroxyhexyl)-3,7-dimethylxanthineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Produkt 1

HCID 232959731-(5-Acetoxy-6-bromohexyl)-3,7-dimethylxanthineAusbeute 96 %

Versuchsvorschrift

To 1-(5,6-dihydroxyhexyl)-3,7-dimethylxanthine (1.0 g, 3.38mmol), prepared above, was added 30% hydrogen bromide-acetic acid (3.4 ml) over 30 sec and the resulting mixture was stirred until all of the solid had dissolved (2.5 hr). The solution was poured carefully over a mixture of sodium bicarbonate (12 gm) and ice water (50 ml). After carbon dioxide evolution had subsided, the mixture was extracted with dichloromethane (3×25 ml). The combined extracts were dried over magnesium sulfate and the solvent was evaporated under vacuum to give 1-(5-acetoxy-6-bromohexyl)-3,7-dimethylxanthine (1.3 g, 96% yield) as a viscous oil which was dissolved in methanol (5 ml). A 1M solution of sodium methoxide in methanol (3.9 ml) was added over 30 sec. After stirring for 20 min, the solution was treated with water (20 ml) and then extracted with dichloromethane (3×15 ml). The combined extracts were dried over magnesium sulfate and the solvents were evaporated under vacuum to give 1-(5,6-oxidohexyl)-3,7-dimethylxanthine (900 mg, 100% yield) as white crystals.

Aufarbeitung

  1. dissolutionhad dissolved (2.5 hr)
  2. extractionthe mixture was extracted with dichloromethane (3×25 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthe solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-932d95e5dabf477aad7dc868c36a02bc
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020337

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