1H-1,2,4-Triazole → 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 1033727Notes

Reaction equation

HRID 1033727 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(#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

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 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 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture consisting of 3.0 g (7.3 mmol) of (+)-3-(6-chloropyridazin-3-ylthio)-2-(2,4-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 2.0 g(29 mmol) of 1,2,4-triazole, and 1.5 ml of acetonitrile was heated at reflux for 19 hours. After allowing the mixture to cool, the solvent was removed by distillation under reduced pressure, and the residue was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The organic layer was washed successively with water and a saturated sodium chloride aqueous solution and dried. The solvent was distilled off 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 from the effluent by distillation under reduced pressure, and the residue was recrystallized from a mixed solvent of chloroform and diethyl ether to obtain 3.0 g (93%) 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 19 hours
  3. temperatureto cool
  4. customthe solvent was removed by distillation under reduced pressure
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed successively with water
  7. dry with materiala saturated sodium chloride aqueous solution and dried
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe solvent was removed from the
  10. distillationeffluent by distillation under reduced pressure
  11. customthe residue was recrystallized from a mixed solvent of chloroform and diethyl ether

Sources & evidence

ORD record
ord-4fbb1dfd273447159f05a118568b6fb8
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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