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

HRID 1684550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684550
[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, 3.38 mmol) was added 30% hydrogen bromide-acetic acid (3.4 ml) over 30 seconds and then stirred until all of the solid had dissolved (2.5 hours). The solution was poured carefully over a mixture of sodium bicarbonate (12 g) 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 seconds. After stirring for 20 minutes, 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 hours)
  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-6d3db5f53c58485a898f3a8dd1420712
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641783

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