Hydrogen Peroxide → Fipronil sulfone

HRID 2188539Notes

Reaction equation

HRID 2188539 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=[O:22].[OH:27]O.O>C(O)(=O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:25])([F:24])[F:26])(=[O:27])=[O:22]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3352Fipronil

Product 1

HCID 3078139Fipronil sulfoneYield 110.3%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 176Acetic AcidSolvent

Procedure

0.17 g (0.4 mmol) of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl) phenyl)-4-((trifluoromethyl) sulfinyl)-1H-pyrazol-3-carbonitrile, 0.01 g (0.03 mmol) of sodium tungstate.2H2O, and 0.07 g (0.6 mmol) of 30% aqueous hydrogen peroxide were dissolved in 1 mL acetic acid and reacted at 55° C. for 6 hours. The reaction solution was cooled, 10 mL water was added, and the reaction mixture was extracted twice with 10 mL ethyl acetate. The ethyl acetate layer was washed with water, then dehydrated over anhydrous magnesium sulfate, filtered and concentrated to give 0.2 g pale yellow crystal of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl) phenyl)-4-((trifluoromethyl) sulfonyl)-1H-pyrazol-3-carbonitrile.

Workup

  1. customreacted at 55° C. for 6 hours
  2. temperatureThe reaction solution was cooled
  3. extractionthe reaction mixture was extracted twice with 10 mL ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f347e622bc543babf746a6330d1acb8
Source dataset
uspto-grants-2012_12
Patent number
US08323904B2

Reaction notes

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