Methanol → 4-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-1H-pyrazole

HRID 1080484Notes

Reaction equation

HRID 1080484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20](SC)=[CH:19][CH:18]=3)=[N:10][NH:11][C:12]=2[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.O[O:26][S:27]([O-:29])=O.[K+].[CH3:31]O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20]([S:27]([CH3:31])(=[O:29])=[O:26])=[CH:21][CH:22]=3)=[N:10][NH:11][C:12]=2[C:13]([F:14])([F:16])[F:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 153802214-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 153802224-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-1H-pyrazoleYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the pyrazole from Step 2 (4.0 g, 11.4 mmol) in 150 mL methanol was added a solution of Oxone® (14.0 g, 22.7 mmol) in 50 mL water. After 1 hour the solids were filtered off, washed with ethyl acetate and the filtrate concentrated in vacuo. This mixture was partitioned between ethyl acetate and water, and the organic layer washed with brine, dried over MgSO4 and reconcentrated in vacuo. Recrystallization from chloroform gave 4-(4-fluorophenyl)-3-[4(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole (3.98 g, 91%) as a pale yellow solid: mp 219°-220° C. Elemental analysis for C17H12N2F4SO2Calc'd.: C, 53.12, H, 3.15, N, 7.29, S, 8.34. Found: C, 52.85, H, 3.12, N, 7.21, S, 8.61

Workup

  1. filtrationAfter 1 hour the solids were filtered off
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customThis mixture was partitioned between ethyl acetate and water
  5. washthe organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-c039c3674fca4ee18785d889d97d23fa
Source dataset
uspto-grants-1996_12
Patent number
US05580985

Reaction notes

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