m-Chloroperbenzoic acid → Benzenesulfonamide

HRID 440061Notes

Reaction equation

HRID 440061 reaction equation
CSC1C=CC(C2N([C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)N=C(C(F)F)C=2)=CC=1.ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl.O>[C:17]1([S:20]([NH2:23])(=[O:22])=[O:21])[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10294097HCID 10294097, compound

Product 1

HCID 7370Benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-[5-(4-[Methylthio]phenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (0.5 g, 1.27 mmol) was dissolved in methylene chloride (30 mL) and cooled to 0° C. To this solution was added m-chloroperoxybenzoic acid (MCPBA) (60%, 0.77 g, 2.7 mmol) and the solution was allowed to warm to room temperature while stirring for 18 hours. A solution of Na2S2O5 (2 g) in H2O (25 mL) was added to the reaction mixture and the solution stirred vigorously for 0.5 hour. The layers were separated and the organic layer was washed with saturated NaHCO3 (30 mL) and brine (30 mL), dried over Na2SO4 and concentrated to yield 4-[5-4-[methylsulfonyl]phenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide as a white solid, 0.22 g, 40%, mp=209°-210° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringthe solution stirred vigorously for 0.5 hour
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated NaHCO3 (30 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f1344bc3c4c448948580a18aad28a267
Source dataset
uspto-grants-1996_05
Patent number
US05516907

Reaction notes

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