Sodium Sulfite → 3-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfonylpyrazole

HRID 1598515Notes

Reaction equation

HRID 1598515 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.ClC1C=C(C(F)(F)F)C=C(Cl)C=1C1C=C(SC)N(C)N=1.[Cl:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([Cl:43])[C:34]=1[C:44]1[CH:48]=[C:47]([S:49]([CH3:51])=[O:50])[N:46]([CH3:52])[N:45]=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:43][C:35]1[CH:36]=[C:37]([C:39]([F:42])([F:40])[F:41])[CH:38]=[C:33]([Cl:32])[C:34]=1[C:44]1[CH:48]=[C:47]([S:49]([CH3:51])(=[O:9])=[O:50])[N:46]([CH3:52])[N:45]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 189294013-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfinylpyrazoleHCID 189294193-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenylpyrazole

Product 1

HCID 189294243-(2,6-Dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfonylpyrazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 0.3 g quantity of 70% m-chloroperbenzoic acid was slowly added to 0.2 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenylpyrazole (compound 6) in 20 ml of anhydrous chloroform at room temperature with stirring, followed by further stirring overnight. The reaction mixture was poured into a 10% aqueous sodium sulfite solution, 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 further stirring overnight
  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-98a0b3bab57c4faf8f1f3a06795f6f04
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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