1,2-Dichloroethane → HCID 19932051, compound

HRID 21601Notes

Reaction equation

HRID 21601 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]([CH2:32][CH3:33])[C:15]([N:17]1[CH:21]=[CH:20][C:19](SC2C(C)=CC=CC=2CC)=[N:18]1)=[O:16])[CH3:13].[S:34]([O-:37])([O-])=[O:35].[Na+].[Na+].Cl[CH2:41][CH2:42]Cl>>[CH2:32]([N:14]([CH2:12][CH3:13])[C:15]([N:17]1[CH:21]=[CH:20][C:19]([S:34]([C:3]2[C:4]([CH3:5])=[CH:9][CH:10]=[CH:11][C:2]=2[CH2:41][CH3:42])(=[O:37])=[O:35])=[N:18]1)=[O:16])[CH3:33]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19931947HCID 19931947, compound

Product 1

HCID 19932051HCID 19932051, compoundYield 99%

Conditions

Temperature
50 °C

Procedure

366 mg of 3-chloroperoxybenzoic acid were added to a solution of 245 mg of 1-(diethylcarbamoyl)-3-(2-ethyl-6methylphenylthio)pyrazole [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 hour. At the end of this time, the reaction mixture was mixed with an aqueous solution of sodium sulfite, after which it was extracted with methylene chloride. The extract was washed with an aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, eluted with an 8:1 by volume mixture of hexane and ethyl acetate, to give 266 mg (yield 99%) of the title compound as an oil.

Workup

  1. extractionafter which it was extracted with methylene chloride
  2. washThe extract was washed with an aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue 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-26a543edb6224d99b8d1a2d4d1dfadd5
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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