1,2-Dichloroethane → 1-(Diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-formylpyrazole

HRID 21605Notes

Reaction equation

HRID 21605 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OO)=O.[CH2:12]([N:14]([CH2:33][CH3:34])[C:15]([N:17]1[CH:21]=[C:20]([CH:22]=[O:23])[C:19](SC2C=CC=C(Cl)C=2C)=[N:18]1)=[O:16])[CH3:13].[S:35]([O-:38])([O-])=[O:36].[Na+].[Na+].[Cl:41]CCCl>>[CH2:33]([N:14]([CH2:12][CH3:13])[C:15]([N:17]1[CH:21]=[C:20]([CH:22]=[O:23])[C:19]([S:35]([C:9]2[CH:10]=[CH:11][CH:2]=[C:3]([Cl:41])[C:4]=2[CH3:5])(=[O:38])=[O:36])=[N:18]1)=[O:16])[CH3:34]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19931920HCID 19931920, compound

Product 1

HCID 199319281-(Diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-formylpyrazoleYield 32%

Procedure

0.77 g of 3-chloroperoxybenzoic acid was added to a solution of 0.57 g of 1-(diethylcarbamoyl)-3-(2-methyl-3-chlorophenylthio)-4-formylpyrazole [prepared as described in step (2) above] in 15 ml of 1,2-dichloroethane, and the resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was then mixed with 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 198 mg (yield 32%) of the title compound, melting at 95°-97° C.

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-4aad46fe95a644ae8e856b6e3a40ad12
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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