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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
Notes
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Reaction equation

HRID 1033728 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 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-olYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d965b42febd84260ae16d92da33a942e
Source dataset
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05312815

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes