m-Chloroperbenzoic acid → 3-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfinylpyrazole

HRID 1598514Notes

Reaction equation

HRID 1598514 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[C:24]1[CH:28]=[C:27]([S:29][CH3:30])[N:26]([CH3:31])[N:25]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:23][C:15]1[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=[C:13]([Cl:12])[C:14]=1[C:24]1[CH:28]=[C:27]([S:29]([CH3:30])=[O:9])[N:26]([CH3:31])[N:25]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 189294193-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenylpyrazole2×

Product 1

HCID 189294013-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfinylpyrazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 0.3 g quantity of 70% m-chloroperbenzoic acid was slowly added to 0.3 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenylpyrazole (compound 1) in 20 ml of anhydrous chloroform at room temperature with stirring, followed by stirring for 3 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, an organic layer was then separated off, washed with 5% aqueous sodium hydroxide solution and with brine and dried over anhydrous magnesium sulfate. The solvent was thereafter distilled off under reduced pressure, giving 0.3 g of the desired compound in the form of white crystals (quantitative crude yield).

Workup

  1. stirringby stirring for 3 hours
  2. customan organic layer was then separated off
  3. washwashed with 5% aqueous sodium hydroxide solution and with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was thereafter distilled off under reduced pressure

Sources & evidence

ORD record
ord-e03c7faaf81e4a7a84f8aef0f783f330
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

Loading…