Water → HCID 15453099, compound

HRID 1603287Notes

Reaction equation

HRID 1603287 reaction equation
[F:1][C:2]([F:21])([S:19][CH3:20])[C:3]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])([OH:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.ClC1C=CC=C(C(OO)=[O:30])C=1.O>C(Cl)Cl>[F:21][C:2]([F:1])([S:19]([CH3:20])=[O:30])[C:3]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])([OH:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 10853188HCID 10853188, compound

Product 1

HCID 15453099HCID 15453099, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 ml solution of 150 mg (0.47 mmol) of 3,3-difluoro-2-(2',4'-difluorophenyl)-3-methylthio-1-(1H-1,2,4-triazol-1-yl)propan-2-ol [Compound (1a-1)] in methylene chloride, 114 mg (0.56 mmol) of m-chloroperbenzoic acid were added at room temperature, followed by stirring for 30 minutes. To the reaction mixture, water was added, followed by extraction with chloroform. The extract was then washed successively with a 10% aqueous solution of sodium thiosulfate and a 10% aqueous solution of sodium carbonate, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The oil so obtained was purified by chromatography on a silica gel column using chloroform : methanol (10:1), whereby 64 mg of the title Compound (1b-1) [diastereomers (1b-1A):(1b-1B)=2.5:1] were obtained in the form of colorless crystals (yield: 40%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe extract was then washed successively with a 10% aqueous solution of sodium thiosulfate
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe oil so obtained
  6. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2261b3f16d3b4eebb54126f9c63f7720
Source dataset
uspto-grants-1999_11
Patent number
US05986144

Reaction notes

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