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Benzyl Bromide → 7-Benzyl-3,8-dimethylxanthine

HRID 1835703
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1835703
[OH-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[C:10]([CH3:13])[NH:9][C:8]=2[C:7](=[O:14])[NH:6][C:5]1=[O:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O.CO>[CH2:16]([N:9]1[C:8]2[C:7](=[O:14])[NH:6][C:5](=[O:15])[N:4]([CH3:3])[C:12]=2[N:11]=[C:10]1[CH3:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 179959183,8-Dimethyl-3,7-dihydro-1H-purine-2,6-dione

Produkt 1

HCID 147126087-Benzyl-3,8-dimethylxanthine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of sodium hydroxide (400 mg) in water (5 ml) was added to a suspension of 3,8-dimethylxanthine (1.80 g) in methanol (10 ml). After stirring for 1 hour at 70° C., benzyl bromide (1.2 ml) was added. After stirring for 5 hours at 70-80° C., the solvent was evaporated under reduced pressure. The residue was treated with saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (30 ml), dried over magnesium sulfate and concentrated under reduced pressure. The solid was purified by recrystallization from ethanol to provide 7-benzyl-3,8-dimethylxanthine (1.06 g).

Aufarbeitung

  1. stirringAfter stirring for 5 hours at 70-80° C.
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was treated with saturated aqueous ammonium chloride solution (50 ml)
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution (30 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe solid was purified by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-df167e1cbe5f4988b8f7c8480d437196
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06774130B2

Notizen zur Reaktion

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