4-Hydrazinylbenzenesulfonamide hydrochloride → 4-[4,5-Dihydro-7-methyl-3-(trifluoromethyl)-1h-benz[g]indazol-1-yl]benzenesulfonamide

HRID 1941703Notes

Reaction equation

HRID 1941703 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][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=O)[CH:20]([C:26](=O)[C:27]([F:30])([F:29])[F:28])[CH2:19][CH2:18]2>C(O)C>[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:21]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:26]([C:27]([F:28])([F:29])[F:30])[C:20]=3[CH2:19][CH2:18][C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 223155526-Methyl-2-(trifluoroacetyl)tetralone

Product 1

HCID 120828204-[4,5-Dihydro-7-methyl-3-(trifluoromethyl)-1h-benz[g]indazol-1-yl]benzenesulfonamideYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Sulfonamidophenylhydrazine hydrochloride (1.80 g, 8.0 mmol) was added to a stirred solution of the diketone from Step 1 (1.86 g, 7.3 mmol) in ethanol (10 mL). The reaction was heated to reflux and stirred for 14.8 hours. The reaction mixture was cooled and filtered. The filtrate was concentrated in vacuo, dissolved in ethyl acetate, washed with water and with brine, dried over MgSO4 and reconcentrated in vacuo to give the pyrazole as a brown solid (1.90 g, 64%): mp 215°-218° C. 1H NMR (acetone-d6) 300 MHz 8.10 (d, 2H), 7.80 (d, 2H), 7.24 (s, 1H), 6.92 (d, 1H), 6.79 (br s, 2H), 6.88 (d,1H), 3.02 (m, 2H), 2.85 (m, 2H), 2.30 (s, 3H). 19F NMR (acetone-d6) 282 MHz −62.46 (s). High resolution mass spectrum Calc'd. for C19H17F3O2S: 408.0994. Found: 408.0989.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutiondissolved in ethyl acetate
  7. washwashed with water and with brine
  8. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-90dd72c571e345528e4c6706ba1be763
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Reaction notes

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