4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 9932059, compound

HRID 1939305Notes

Reaction equation

HRID 1939305 reaction equation
[CH:1]1[C:6]([NH:7][NH2:8])=[CH:5][CH:4]=[C:3]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:2]=1.Cl.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=O)[C:21](=[C:27](O)[C:28]([F:31])([F:30])[F:29])[CH2:20][CH2:19]2>C(O)C>[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:23]2[C:22]3[N:7]([C:6]4[CH:1]=[CH:2][C:3]([S:9]([NH2:12])(=[O:10])=[O:11])=[CH:4][CH:5]=4)[N:8]=[C:27]([C:28]([F:30])([F:29])[F:31])[C:21]=3[CH2:20][CH2:19][C:18]=2[CH:17]=1

Participants

4

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 178487170HCID 178487170, compound

Product 1

HCID 9932059HCID 9932059, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Sulfonamidophenylhydrazine hydrochloride (4.35 g, 19.4 mmol) was added to a stirred solution of 3,4-dihydro-6-methoxy-2-[2,2,2-trifluoro-1-hydroxyethylidene]-1(2H)-naphthalenone from Step 1 (5.06 g, 18.6 mmol) in ethanol (100 mL). The reaction was heated to reflux and stirred for 16 hours. The reaction mixture was filtered and washed with ethanol to give the desired pyrazole as a white solid (6.97 g, 88%): mp 277°-278° C.; 1H NMR (acetone d6) 300 MHz 8.09 (d, J=8.7 Hz, 2H) 7.80 (d, J=8.9 Hz, 2H) 7.00 (d, J=2.6 Hz, 1H) 6.78 (m, 3H) 6.69 (dd, J=8.7 Hz J=2.6 Hz, 1H) 3.81 (s, 3H) 3.04 (m, 2H) 2.84 (m, 2H); 19F NMR (acetone d6) 300 MHz -62.43 (s). Mass Spectrum M+ =423.0838.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-17d33de65f974544a70289a6dd822276
Source dataset
uspto-grants-1997_12
Patent number
US05696143

Reaction notes

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