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Sodium Iodide → 2-(2,4-Difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-3-{[6-(1H-1,2,4-triazol-1-yl)pyridazin-3-yl]sulfanyl}butan-2-ol

HRID 1033728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1033728
Cl[C:2]1[N:7]=[N:6][C:5]([S:8][C:9]([CH3:27])([CH3:26])[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])([OH:17])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:4][CH:3]=1.[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C:10]([OH:17])([C:9]([CH3:27])([S:8][C:5]1[N:6]=[N:7][C:2]([N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)=[CH:3][CH:4]=1)[CH3:26])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19024386HCID 19024386, Verbindung

Produkt 1

HCID 1278122-(2,4-Difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-3-{[6-(1H-1,2,4-triazol-1-yl)pyridazin-3-yl]sulfanyl}butan-2-olAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture consisting of 1.6 g (3.9 mmol) of (+)-3-(6-chloropyridazin-3-ylthio)-2-(2,4-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 1.0 g (14.5 mmol) of 1,2,4-triazole, 1.0 g (7.2 mmol) of potassium carbonate, 2.2 g (14.7 mmol) of sodium iodide, and 20 ml of acetonitrile was heated at reflux for 116 hours. After allowing the mixture to cool, the solvent was removed by distillation under reduced pressure, and to the residue was added a saturated sodium chloride aqueous solution, followed by extraction with dichloromethane. The organic layer was washed successively with 10% sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution and dried. The solvent was removed by distillation under reduced pressure, and the residue was subjected to column chromatography using a mixed solvent of chloroform and methanol (100:1). The solvent was removed by distillation under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and methanol to obtain 1.2 g (70%) of (+)-2-(2,4-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-3-(6-(1H-1,2,4-triazol-1-yl)pyridazin-3-ylthio)butan-2-ol as a colorless crystal.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 116 hours
  3. temperatureto cool
  4. customthe solvent was removed by distillation under reduced pressure
  5. additionto the residue was added a saturated sodium chloride aqueous solution
  6. extractionfollowed by extraction with dichloromethane
  7. washThe organic layer was washed successively with 10% sodium thiosulfate aqueous solution
  8. dry with materiala saturated sodium chloride aqueous solution and dried
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe solvent was removed by distillation under reduced pressure
  11. customthe residue was recrystallized from a mixed solvent of isopropyl ether and methanol

Quellen und Nachweise

ORD-Eintrag
ord-d965b42febd84260ae16d92da33a942e
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05312815

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