4-Hydrazinylbenzenesulfonamide hydrochloride → 4-[5-[4-(2-Furyl)-3-methylphenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenylsulfonamide

HRID 396740Notes

Reaction equation

HRID 396740 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([CH3:18])[CH:8]=1)=O.Cl.[S:23]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=1)(=[O:26])(=[O:25])[NH2:24]>C(O)C>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:33]([C:30]3[CH:29]=[CH:28][C:27]([S:23]([NH2:24])(=[O:26])=[O:25])=[CH:32][CH:31]=3)[N:34]=[C:3]([C:2]([F:21])([F:20])[F:1])[CH:4]=2)=[CH:8][C:9]=1[CH3:18]

Participants

4

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 223167484,4,4-Trifluoro-1-[4-(2-furyl)-3-methylphenyl]butane-1,3-dione

Product 1

HCID 223169494-[5-[4-(2-Furyl)-3-methylphenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenylsulfonamideYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred soluition of 4,4,4-trifluoro-1-[4-(2-furyl)-3-methylphenyl]butane-1,3-dione (0.53 g, 1.80 mmol) in ethanol (22.5 ml) was added (4-sulfamoylphenyl)hydrazine hydrochloride (0.44 ml, 1.98 mmol), and the mixture was heated at reflux temperature for 16 hours. The mixture was cooled down to room temperature, and concentrated in vacuo. The residue was dissolved in ethyl acetate. washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1/3). The resulting solid was recrystallized with dichloromethane-hexane to give the title compound (0.16 g, 20% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate/hexane (1/3)
  10. customThe resulting solid was recrystallized with dichloromethane-hexane

Sources & evidence

ORD record
ord-67d5e7a112894b58a7b9e1c3daaf64e4
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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