تفاعل #2028890

معادلة التفاعل

4-[5-(4-chlorophenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

acetic acid

chlorine

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4-[5-(4-chlorophenyl)-4-chloro-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

المردود 75.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىA 100 mL three-necked round-bottomed flask equipped
2. 2
   درجة الحرارةwith reflux condenser, gas dispersion tube
3. 3
   workup.STIRRINGThe solution was stirred at room temperature
4. 4
   workup.STIRRINGThe solution was then stirred at room temperature for 1.25 hours
5. 5
   استخلاصThe solution was then extracted three times with ether
6. 6
   غسيلthe combined ethereal phase washed with brine
7. 7
   تجفيفdried over MgSO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىto give a white solid
11. 11
    أخرىthat was recrystallized from ether/petroleum ether

الإجراء التجريبي

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=6.6Hz, 2H, 7.49 (d, 2H), 7.45 (d, J=6.3Hz, 2H), 7.25 (d, J=6.6Hz, 2H), 5.78 (brs, 2H).

المصدر