Benzyl Bromide → 7-Benzyl-3-butylxanthine

HRID 323853

Reaktionsgleichung

Reaktionsgleichung von HRID 323853
[OH-].[Na+].[CH2:3]([N:7]1[C:15]2[N:14]=[CH:13][NH:12][C:11]=2[C:10](=[O:16])[NH:9][C:8]1=[O:17])[CH2:4][CH2:5][CH3:6].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CO>[CH2:18]([N:12]1[C:11]2[C:10](=[O:16])[NH:9][C:8](=[O:17])[N:7]([CH2:3][CH2:4][CH2:5][CH3:6])[C:15]=2[N:14]=[CH:13]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl Bromide2×HCID 14798Sodium Hydroxide2×HCID 2186671H-Purine-2,6-dione, 3,7-dihydro-3-butyl-

Produkt 1

HCID 39938667-Benzyl-3-butylxanthine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

10 g (0.25 mol) of sodium hydroxide dissolved in 100 ml of water were added to a suspension of 52 g (0.25 mol) of 3-butylxanthine in 300 ml of methanol and the reaction mixture was stirred at 70° C. for one hour, then treated dropwise at the same temperature with 42.8 g (0.25 mol) of benzyl bromide and kept between 70° and 80° C. for 5 hours. 1.0 g (0.025 mol) of sodium hydroxide and 4.28 g (0.025 mol) of benzyl bromide were then added. After a further 2 hours, the mixture was cooled, diluted with 1500 ml of water and filtered cold on a suction filter, the product was washed with water on the suction filter and dissolved in 1000 ml of 1 N sodium hydroxide solution, and the solution was filtered and slowly brought to pH 3 with stirring using concentrated hydrochloric acid. The crystallizate was filtered off from the solution, washed with water until chloride-free and dried under reduced pressure.

Aufarbeitung

  1. waitkept between 70° and 80° C. for 5 hours
  2. waitAfter a further 2 hours
  3. temperaturethe mixture was cooled
  4. filtrationfiltered cold on a suction
  5. filtrationfilter
  6. washthe product was washed with water on the suction
  7. filtrationfilter
  8. dissolutiondissolved in 1000 ml of 1 N sodium hydroxide solution
  9. filtrationthe solution was filtered
  10. stirringwith stirring
  11. filtrationThe crystallizate was filtered off from the solution
  12. washwashed with water until chloride-free
  13. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-be0c83a3a4894dbaba00268796799358
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214992B1

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