Réaction #2028878

Équation de réaction

4,4-Dichloro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione

4-sulfonamidophenylhydrazine hydrochloride

water

→

solid

Rendement 63.0%

4-[3-(dichloromethyl)-5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-1-yl]benzenesulfonamide

Rendement 63.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureto reflux for 16 hours
3. 3
   TempératureThe mixture was cooled
4. 4
   FiltrationFiltration

Mode opératoire

4,4-Dichloro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione from Step 2 (2.8 g, 10 mmol) was dissolved in ethanol (100 mL). To the stirred mixture was added 4-sulfonamidophenylhydrazine hydrochloride (2.46 g, 11 mmol) and heated to reflux for 16 hours. The mixture was cooled and water was added until crystals slowly appeared. Filtration yielded a light tan solid (2.7 g, 63%): mp 190°-193° C.: 1H NMR (DMSO-d6) 7.84 (d, J=8.4Hz, 2H), 7.53 (s, 1H), 7.48 (d, J=8.4Hz, 2H), 7.47 (brs, 2H), 7.3-7.0 (m, 3H), 6.95 (s, 1H), 3.85 (s, 3H). Anal. Calc'd for C17H14N3SO3FCl2: C, 47.45; H, 3.28; N, 9.76. Found: C, 47.68; H, 3.42; N, 10.04.

Source