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

HRID 1941706Notes

Reaction equation

HRID 1941706 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[CH:13]1[C:18]([NH:19][NH2:20])=[CH:17][CH:16]=[C:15]([S:21]([NH2:24])(=[O:23])=[O:22])[CH:14]=1.Cl.N1C=CC=N1>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:19]([C:18]3[CH:13]=[CH:14][C:15]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:16][CH:17]=3)[N:20]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 104423563-(4-Chlorophenyl)-3-oxopropanal

Product 1

HCID 108305124-[5(4-chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamideYield 25.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. customformed
  4. customthat were isolated by filtration

Sources & evidence

ORD record
ord-a3509b647b3842c88b265ff08cce847b
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Reaction notes

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