1,2-Dichloroethane → HCID 19932273, compound

HRID 21604Notes

Reaction equation

HRID 21604 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]([CH2:34][CH3:35])[C:15]([N:17]1[CH:21]=[C:20]([O:22][CH3:23])[C:19](SC2C(CC)=CC=CC=2C)=[N:18]1)=[O:16])[CH3:13].[S:36]([O-:39])([O-])=[O:37].[Na+].[Na+].Cl[CH2:43][CH2:44]Cl>>[CH2:34]([N:14]([CH2:12][CH3:13])[C:15]([N:17]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([S:36]([C:5]2[C:4]([CH2:9][CH3:10])=[CH:3][CH:2]=[CH:11][C:43]=2[CH3:44])(=[O:39])=[O:37])=[N:18]1)=[O:16])[CH3:35]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19931912HCID 19931912, compound

Product 1

HCID 19932273HCID 19932273, compoundYield 51%

Conditions

Temperature
50 °C

Procedure

84 mg of 3-chloroperoxybenzoic acid were added to a solution of 62 mg of 1-(diethylcarbamoyl)-3-(2-methyl-6-ethylphenylthio)-4-methoxypyrazole [prepared as described in step (4) above] in 2 ml of 1,2-dichloroethane, and the resulting mixture was stirred at 50° C. for 2 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 a 7:1 by volume mixture of hexane and ethyl acetate, to afford 34 mg (yield 51%) 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 a 7:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-a2178be7daef498ca5f41ea0b004e863
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

Loading…