Reaktion #2028888

Reaktionsgleichung

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

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

4-sulfonamidophenylhydrazine hydrochloride

pyrazole

→

white solid

Ausbeute 25.2%

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

Ausbeute 25.2%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 16 hours
3. 3
   Sonstigeformed
4. 4
   Sonstigethat were isolated by filtration

Vorschrift

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.

Quelle