Water → 6-Chloro-2-(2-cyanoethyl)-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on

HRID 27000

Reaktionsgleichung

Reaktionsgleichung von HRID 27000
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.CC(C)([O-])C.[K+].[C:18](#[N:21])[CH:19]=[CH2:20].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[N:9]([CH2:20][CH2:19][C:18]#[N:21])[N:10]=2)[N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7855AcrylonitrileHCID 64071826-chloro-2H,3H-[1,2,4]triazolo[4,3-b]pyridazin-3-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 203443466-Chloro-2-(2-cyanoethyl)-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-onAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 6-chloro-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on [P. Francabilla and F. Lauria, J. Het. Chem. 8, 415 (1971)] (17 g., 0.1 mole) in dry DMF (300 ml.) was added potassium tert.-butoxide (0.5 g., 4.5 m.moles) with stirring. Acrylonitrile (6.6 g., 0.12 mole) in dry DMF (10 ml.) was added to the mixture. The mixture was stirred at 100°-110° C. for 24 hours, then poured into water (700 ml.) and extracted with ethyl acetate (5×400 ml.). The organic extracts were combined, dried over Na2SO4 and evaporated. The residue was crystallized from ethyl acetate to give light yellow needles of 6-chloro-2-(2-cyanoethyl)-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on (2.5 g., 11%). M.p. 166°-168° C.

Aufarbeitung

  1. stirringThe mixture was stirred at 100°-110° C. for 24 hours
  2. extractionextracted with ethyl acetate (5×400 ml.)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-21dc73c207a544c48b3b88e1c2f6a716
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151352

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