Sodium Sulfite → HCID 19932259, compound

HRID 21608Notes

Reaction equation

HRID 21608 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)C(OO)=O.[CH2:12]([N:14]([CH2:33][CH3:34])[C:15]([N:17]1[CH:21]=[C:20]([CH:22]([F:24])[F:23])[C:19](SC2C=CC=C(Cl)C=2)=[N:18]1)=[O:16])[CH3:13].[S:35]([O-:38])([O-])=[O:36].[Na+].[Na+]>ClCCCl>[CH2:33]([N:14]([CH2:12][CH3:13])[C:15]([N:17]1[CH:21]=[C:20]([CH:22]([F:23])[F:24])[C:19]([S:35]([C:4]2[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)(=[O:38])=[O:36])=[N:18]1)=[O:16])[CH3:34]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19932026HCID 19932026, compound

Product 1

HCID 19932259HCID 19932259, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

250 mg of 3-chloroperoxybenzoic acid were added to a solution of 179 mg of 1-(diethylcarbamoyl)-3-(3-chlorophenylthio)-4-difluoromethylpyrazole [prepared as described in step (4) above] in 4 ml of 1,2-dichloroethane, and the resulting mixture was heated at 50° C. for 1.5 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium sulfite and extracted with methylene chloride. The extract was washed with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, eluted with an 8:1 by volume mixture of hexane and ethyl acetate, to afford 170 mg (yield 87%) of the title compound as an oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialafter which it was dried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe concentrate was purified by column chromatography through silica gel
  6. washeluted with an 8:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-5d83b2dbbfa14e40a34eeacee5cb08df
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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