1,2-Dichloroethane → HCID 19931851, compound

HRID 21603Notes

Reaction equation

HRID 21603 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[C:21](SC2C=C(C)C=CC=2C)=[C:20]([Br:31])[CH:19]=[N:18]1)=[O:16])[CH3:13].[S:34]([O-:37])([O-])=[O:35].[Na+].[Na+].Cl[CH2:41]CCl>>[CH2:12]([N:14]([CH2:32][CH3:33])[C:15]([N:17]1[CH:21]=[C:20]([Br:31])[C:19]([S:34]([C:2]2[CH:3]=[C:4]([CH3:5])[CH:9]=[CH:10][C:11]=2[CH3:41])(=[O:37])=[O:35])=[N:18]1)=[O:16])[CH3:13]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19932053HCID 19932053, compound

Product 1

HCID 19931851HCID 19931851, compoundYield 83%

Conditions

Temperature
50 °C

Procedure

398 mg of 3-chloroperoxybenzoic acid were added to a solution of 315 mg of 1-(diethylcarbamoyl)-4-bromo-5-(2,5-dimethylphenylthio)pyrazole [prepared as described in step (2) above] in 7 ml of 1,2-dichloroethane, and the resulting mixture was heated at 50° C. for 2 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 water, in that order, after which it was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, eluted with a 10:1 by volume mixture of hexane and ethyl acetate, to give 283 mg (yield 83%) of the title compound, melting at 82°-83° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with an aqueous solution of sodium hydrogencarbonate and with water, in that order
  3. dry with materialafter which it was dried 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 a 10:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e6be7856bc9b4f418048b87e6ac4b152
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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