Acetic Acid → HCID 10296709, compound

HRID 2084720Notes

Reaction equation

HRID 2084720 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 (Example 1) (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 MgSO4, filtered, and concentrated in vacuo to give a white 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. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a white solid
  11. customthat was recrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-3c40428ce3db4fd196e3b274c224b469
Source dataset
uspto-grants-2004_04
Patent number
US06716991B1

Reaction notes

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