반응 #2028889

반응 방정식

4-[5-(4-Chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamide

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

chlorine

sodium bicarbonate

→

white solid

수율 78.0%

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

수율 78.0%

용매

acetic acid

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONwas slowly added until the mixture
2. 2
   추출The mixture was extracted with ethyl acetate (3×50 mL)
3. 3
   세척washed with sat. aq. sodium bicarbonate and with brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The resultant product was recrystallized from isopropanol

실험 절차

4-[5-(4-Chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamide from Step 2 (3.0 g, 9 mmol) was dissolved in 50 mL of acetic acid, and 9 mL of 1M chlorine in acetic acid was added dropwise. The mixture was stirred for 16 hours when sat. aq. sodium bicarbonate solution was slowly added until the mixture was neutral to pH paper. The mixture was extracted with ethyl acetate (3×50 mL), combined and washed with sat. aq. sodium bicarbonate and with brine, dried over magnesium sulfate, filtered, and concentrated. The resultant product was recrystallized from isopropanol to yield 2.6 g (78%) of a white solid: mp 168°-171° C. (dec); 1H NMR (DMSO-D6/300 MHz) 8.08 (s, 1H), 7.83 (d, J=8.7Hz, 2H), 7.55 (d, J=8.7Hz, 2H), 7.46 (brs, 2H), 7.44 (d, J=8.7Hz, 2H), 7.35 (d, J=8.7Hz, 2H). Anal. Calc'd for C15H11N3SO2Cl2: C, 48.93; H, 3.01; N, 11.41. Found: C, 49.01; H, 2.97; N, 11.41.

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