1H-1,2,4-Triazole → HCID 20079600, compound

HRID 1033737Notes

Reaction equation

HRID 1033737 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)([CH3:14])[CH3:13])[CH2:11][O:10]1.[NH:25]1[CH:29]=[N:28][CH:27]=[N:26]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([C:12]([S:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)([CH3:14])[CH3:13])[CH2:11][N:25]1[CH:29]=[N:28][CH:27]=[N:26]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19024387HCID 19024387, compound

Product 1

HCID 20079600HCID 20079600, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 64.0 g (182 mmol) of (-)-2-(2,4-difluorophenyl)-2-(1-((4-methoxyphenyl)methylthio)-1-methylethyl)oxirane, 25.1 g (364 mmol) of 1,2,4-triazole, 50.3 g (364 mmol) of potassium carbonate, and 910 ml of DMF was stirred at 105° C. for 17 hours. After allowing the mixture to cool, the solvent was removed by distillation under reduced pressure, and to the residue were added dichloromethane and water. The organic layer was separated, washed with a saturated sodium chloride aqueous solution, and dried. The solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography using a mixed solvent of chloroform and methanol (30:1) as an eluent. The solvent was removed by distillation under reduced pressure to obtain 72.0 g (94%) of (+)-2-(2,4-difluorophenyl)-3-((4-methoxyphenyl)methylthio)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol as a pale yellow oily substance.

Workup

  1. temperatureto cool
  2. customthe solvent was removed by distillation under reduced pressure
  3. additionto the residue were added dichloromethane and water
  4. customThe organic layer was separated
  5. washwashed with a saturated sodium chloride aqueous solution
  6. customdried
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by column chromatography
  9. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-af36e9d1059d41739aede6190f4d7d40
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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