Acetic Acid → 5-Methanesulfonyl-1-methyl-3-(trifluoromethyl)pyrazole

HRID 1670369Notes

Reaction equation

HRID 1670369 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([C:9]([F:12])([F:11])[F:10])=[N:3]1.OO.[OH2:15].C(O)(=[O:18])C>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:8][S:7]([C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=1)(=[O:18])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 593563841-Methyl-5-methylthio-3-(trifluoromethyl)pyrazole

Product 1

HCID 593563985-Methanesulfonyl-1-methyl-3-(trifluoromethyl)pyrazole

Reagents, catalysts & solvents 1

HCID 150191Sodium Tungstate DihydrateCatalyst

Procedure

0.25 g of Compounds (14) was dissolved in 20 ml of acetic acid. While stirring, 0.44 g of 30% hydrogen peroxide solution, and 0.04 g of sodium tungstate dihydrate were added sequentially. The mixture was stirred at room temperature for 12 hours, then poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogencarbonate, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to produce 0.29 g of 5-methanesulfonyl-1-methyl-3-(trifluoromethyl)pyrazole (2-1).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium hydrogencarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42b6c6a74d7c4e57b1b24da8832acf29
Source dataset
uspto-grants-2011_08
Patent number
US07994094B2

Reaction notes

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