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

HRID 2227422Notes

Reaction equation

HRID 2227422 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=8.7 Hz, 2H), 7.76 (d, J=1.8 Hz, 1H), 7.43 (d, J=8.7 Hz, 2H), 7.34 (d, J=8.7 Hz, 2H), 7.17 (d, J=8.7 Hz, 2H), 6.53 (d, J=1.8 Hz, 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-a0eb30bda7b549a383303928a6d029c7
Source dataset
uspto-grants-2002_07
Patent number
US06413960B1

Reaction notes

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