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3-[4-(Chloro)phenyl]-propane-1,3-dione

3-[4-(chloro)phenyl]-propane-1,3-dione

4-sulfonamidophenylhydrazine hydrochloride

pyrazole

→

white solid

수율 25.2%

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

수율 25.2%

용매

ethanol

water

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 16 hours
3. 3
   기타formed
4. 4
   기타that were isolated by filtration

실험 절차

3-[4-(Chloro)phenyl]-propane-1,3-dione from Step 1 (18.3 g, 0.1 mol) and 4-sulfonamidophenylhydrazine hydrochloride (22.4 g, 0.1 mol) were dissolved in 150 mL of absolute ethanol and heated to reflux for 16 hours. The solution was cooled to room temperature, diluted with 100 mL of water and let stand, whereupon crystals of pyrazole formed that were isolated by filtration to provide 8.4 g (25%) of a white solid: mp 185°-187° C.; 1H NMR (CDCl3/300 MHz) 7.89 (d, J=8.7Hz, 2H), 7.76 (d, J=1.8Hz, 1H), 7.43 (d,J=8.7Hz, 2H), 7.34 (d, J=8.7Hz, 2H), 7.17 (d, J=8.7Hz, 2H), 6.53 (d, J=1.8Hz, 1H), 4.93 (brs 2H). Anal. Calc'd for C15H12N3SO2Cl: C, 53.97; H, 3.62; N, 12.59. Found: C, 54.08; H, 3.57; N, 12.64.

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