Реакция #2028890

Уравнение реакции

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

acetic acid

chlorine

→

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

Выход 75.0%

Растворители

water

Условия реакции

Обработка

1. 1
   ДругоеA 100 mL three-necked round-bottomed flask equipped
2. 2
   Температураwith 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
   ЭкстракцияThe solution was then extracted three times with ether
6. 6
   Промывкаthe combined ethereal phase washed with brine
7. 7
   Сушкаdried over MgSO4
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated in vacuo
10. 10
    Другоеto give a white solid
11. 11
    Другоеthat was recrystallized from ether/petroleum ether

Методика

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).

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