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

HRID 441048Notes

Reaction equation

HRID 441048 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.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

5

Reactant 3

HCID 702EthanolHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 104423563-(4-Chlorophenyl)-3-oxopropanal

Product 1

HCID 108305124-[5(4-chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL one-necked round-bottomed flask equipped with reflux condenser, nitrogen inlet and provisions for magnetic stirring was charged with 3-(4-chlorophenyl)-3-ketopropionaldehyde (18.3 g, 0.1 mol), 4-sulfonamidophenylhydrazine hydrochloride (11.2 g, 0.05 mol) and 100 mL of absolute ethanol. The solution was heated to reflux for 15 hour and then diluted with 100 mL of water and allowed to stand whereupon a white solid formed that was isolated by filtration on a Buchner funnel and air dried to provide 12.6 g, 76% of 4-[5-(4-chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamide, mp 185°-187° C. 1H nmr (CDCl3 /300MHz ) 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), mass spectrum MH+=334.

Workup

  1. customA 250 mL one-necked round-bottomed flask equipped
  2. temperaturewith reflux condenser, nitrogen inlet
  3. temperatureThe solution was heated
  4. temperatureto reflux for 15 hour
  5. customformed that
  6. customwas isolated by filtration on a Buchner funnel and air
  7. customdried

Sources & evidence

ORD record
ord-6b3766900dfc46cc87ea21128664060d
Source dataset
uspto-grants-1996_05
Patent number
US05521207

Reaction notes

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