Sodium Hydroxide → Propentofylline

HRID 2259588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2259588
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH3:13])[C:6]=2[C:5](=[O:14])[NH:4][C:3]1=[O:15].[OH-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:25])[CH3:24]>CO.O>[O:25]=[C:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][N:4]1[C:5](=[O:14])[C:6]2[N:7]([CH2:11][CH2:12][CH3:13])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:15].[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH3:13])[C:6]=2[C:5](=[O:14])[NH:4][C:3]1=[O:15]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 250616-Bromohexan-2-oneHCID 33143973-Methyl-7-propylpurine-2,6-dione

Produkt 2

HCID 4938PropentofyllineHCID 33143973-Methyl-7-propylpurine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

437.2 g of 3-methyl-7-propylxanthine are suspended in a mixture of 240 g of methanol and 321 g of water and induced to dissolve at elevated temperature with 160 g of 50% strength sodium hydroxide solution, and subsequently at the boiling point 358 g of 1-bromo-5-hexanone are added and the mixture is heated to reflux for 41/2 hours. After cooling, unreacted 3-methyl-7-propylxanthine is separated off and the alcohol is removed by distillation. The aqueous solution is adjusted to pH 11 with sodium hydroxide solution and extracted with methylene chloride. 1-(5-Oxohexyl)-3-methyl-7-propylxanthine is obtained with melting point 69°-70° C. in approximately 90% yield (based on reacted 3-methyl-7-propylxanthine) from the residue of the methylene chloride solution after recrystallization from 5.2 of diisopropyl ether.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 41/2 hours
  3. temperatureAfter cooling
  4. customunreacted 3-methyl-7-propylxanthine is separated off
  5. customthe alcohol is removed by distillation
  6. extractionextracted with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-5371b9480e924e9a9c751bd5242fb330
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05475002

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