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

HRID 1941703

Reaktionsgleichung

Reaktionsgleichung von HRID 1941703
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-90dd72c571e345528e4c6706ba1be763
Quelldatensatz
uspto-grants-2013_03
Patentnummer
USRE044048E1

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