Hydrochloric Acid → 1-Butanesulfonamide, 2-ethyl-2-(((7-methyl(1,2,4)triazolo(1,5-b)pyridazin-6-yl)oxy)methyl)-

HRID 274269

Reaktionsgleichung

Reaktionsgleichung von HRID 274269
CN(C=[N:5][S:6]([CH2:9][C:10]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:11][OH:12])(=[O:8])=[O:7])C.[H-].[Na+].Cl[C:20]1[C:21]([CH3:29])=[CH:22][C:23]2[N:24]([N:26]=[CH:27][N:28]=2)[N:25]=1.Cl>O1CCCC1>[CH2:15]([C:10]([CH2:13][CH3:14])([CH2:9][S:6](=[O:7])(=[O:8])[NH2:5])[CH2:11][O:12][C:20]1[C:21]([CH3:29])=[CH:22][C:23]2[N:24]([N:26]=[CH:27][N:28]=2)[N:25]=1)[CH3:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 536426363-(N,N-dimethylaminomethylene)aminosulfonyl-2,2-diethyl-1-propanol

Produkt 1

HCID 30737861-Butanesulfonamide, 2-ethyl-2-(((7-methyl(1,2,4)triazolo(1,5-b)pyridazin-6-yl)oxy)methyl)-Ausbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.38 g of 3-(N,N-dimethylamino-methylene)aminosulfonyl-2,2-diethyl-1-propanol in 30 ml of tetrahydrofuran was added 0.23 g of 60% sodium hydride in oil and the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added 0.74 g of 6-chloro-7-methyl[1,2,4]triazolo[1,5-b]pyridazine and the mixture was refluxed with stirring for 1 hour. After cooling, the reaction mixture was adjusted to pH 6 with 1N-hydrochloric acid and extracted with ethyl acetate-tetrahydrofuran (1:1). The extract was washed with water and dried and the solvent was distilled off. To the residue was added 14 ml of 6N-hydrochloric acid and the mixture was stirred at 110° C. for 30 minutes. After cooling, 100 ml of water was added to the reaction mixture and the resulting crystals were recovered by filtration and recrystallized from methanol to provide 1.16 g of the title compound. m.p. 208°-209° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. additionTo the residue was added 14 ml of 6N-hydrochloric acid
  9. stirringthe mixture was stirred at 110° C. for 30 minutes
  10. temperatureAfter cooling
  11. addition100 ml of water was added to the reaction mixture
  12. filtrationthe resulting crystals were recovered by filtration
  13. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-fcf291590c6245a5bef8512c7a58119f
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389633

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