1,2-Dichloroethane → HCID 19932173, compound

HRID 21609Notes

Reaction equation

HRID 21609 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OO)=O.[C:12]([C:14]1[C:15](SC2C(C)=CC=CC=2CC)=[N:16][N:17]([C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:18]=1)#[N:13].[S:36]([O-:39])([O-])=[O:37].[Na+].[Na+].Cl[CH2:43][CH2:44]Cl>>[C:12]([C:14]1[C:15]([S:36]([C:3]2[C:4]([CH3:5])=[CH:9][CH:10]=[CH:11][C:2]=2[CH2:43][CH3:44])(=[O:39])=[O:37])=[N:16][N:17]([C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:18]=1)#[N:13]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19932042HCID 19932042, compound

Product 1

HCID 19932173HCID 19932173, compoundYield 95%

Conditions

Temperature
50 °C

Procedure

200 mg of 3-chloroperoxybenzoic acid were added to a solution of 150 mg of 4-cyano-1-(diethylcarbamoyl)-3-(2-ethyl-6-methylphenylthio)pyrazole [prepared as described in step (3) above] in 5 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, 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 6:1 by volume mixture of hexane and ethyl acetate, to afford 153 mg (yield 95%) of the title compound, melting at 101°-102° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with an aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried 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 6:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-0fd94be5176a467686ac36966550e3ae
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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