Glycidol → 6-(2-Oxiranylmethoxy)[1,2,4]triazolo[4,3-b]pyridazine

HRID 397553

Reaktionsgleichung

Reaktionsgleichung von HRID 397553
[O:1]1[CH2:3][CH:2]1[CH2:4][OH:5].Cl[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][N:15]=2)[N:12]=1.[H-].[Na+]>CN(C)C=O>[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][N:15]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 11164GlycidolHCID 24758Sodium hydrideHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazine

Produkt 1

HCID 230003166-(2-Oxiranylmethoxy)[1,2,4]triazolo[4,3-b]pyridazineAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

12.0 g of 2-oxiranylmethanol and 2.50 g of 6-chloro[1,2,4]triazolo[4,3-b]pyridazine were dissolved in 40 ml of N,N-dimethylformamide; under ice cooling, 713 mg of 60% oily sodium hydride was added, followed by stirring at room temperature for 30 minutes. After cold saline was added, the reaction mixture was extracted with ethyl acetate-tetrahydrofuran (1:1) and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (10:1). The desired fraction was collected and concentrated under reduced pressure; the precipitated crystal was washed with diethyl ether and dried to yield 1.02 g of the title compound.

Aufarbeitung

  1. additionAfter cold saline was added
  2. extractionthe reaction mixture was extracted with ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. washeluted with ethyl acetate-methanol (10:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure
  8. washthe precipitated crystal was washed with diethyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8957a2a462814b4bae3c9e5dff4a92b5
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610694B1

Verknüpfte Notizen

Wird geladen…