Acetic Acid → HCID 10296709, compound

HRID 129216Notes

Reaction equation

HRID 129216 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.[Cl:31]Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:24])([F:25])[F:26])[C:9]=2[Cl:31])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24526ChlorineHCID 98658084-(5-(4-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide

Product 1

HCID 10296709HCID 10296709, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL three-necked round-bottomed flask equipped with reflux condenser, gas dispersion tube and provisions for magnetic stirring was charged with 4-[5-(4-chlorophenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide (500 mg, 1.2 mmol) and 50 mL of glacial acetic acid. The solution was stirred at room temperature and treated with a stream of chlorine gas for a period of 15 minutes. The solution was then stirred at room temperature for 1.25 hours and then diluted with 100 mL of water. The solution was then extracted three times with ether and the combined ethereal phase washed with brine, dried over anhyd. MGSO4, filtered, and concentrated in vacuo to give a while solid that was recrystallized from ether/petroleum ether to provide 390 mg, 75% of 4-[5-(4-chlorophenyl)-4-chloro-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide, mp 180°-182° C. 1H nmr (CDCl3 /300 MHz) 7.97(d, J=6.6 Hz, 2H), 7.49(d, J= 6.3 Hz, 2H), 7.45(d, J=6.3 Hz, 2H), 7.25(d, J=6.6 Hz, 2H), 5.78(brs, 2H).

Workup

  1. customA 100 mL three-necked round-bottomed flask equipped
  2. temperaturewith reflux condenser, gas dispersion tube
  3. stirringThe solution was stirred at room temperature
  4. stirringThe solution was then stirred at room temperature for 1.25 hours
  5. extractionThe solution was then extracted three times with ether
  6. washthe combined ethereal phase washed with brine
  7. customdried over anhyd
  8. filtrationMGSO4, filtered
  9. concentrationconcentrated in vacuo
  10. customto give a while solid
  11. customthat was recrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-12692e2ef41b4508b36bccef4d7360cd
Source dataset
uspto-grants-1995_11
Patent number
US05466823

Reaction notes

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