Hydroquinone → 4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

HRID 1939310

Reaktionsgleichung

Reaktionsgleichung von HRID 1939310
[F:1][C:2]([F:27])([F:26])[C:3]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][CH:10]=2)[N:5]([CH:16]2[CH2:21][CH:20]=[C:19]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:18]=[CH:17]2)[N:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(C=CC(O)=CC=1)O>O1CCOCC1>[F:27][C:2]([F:1])([F:26])[C:3]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][CH:10]=2)[N:5]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[N:4]=1

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone3×HCID 189203554,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

Produkt 1

HCID 214675164-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4,5-Dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide from Step 2 (393 mg, 1.0 mmol) was dissolved in 1,4-dioxane (50 ml), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (227 mg, 1.0 mmol) was added. The reaction was heated to reflux for 16 hours at which time a second equivalent of DDQ (227 mg, 1.0 mmol) was added and the reaction was heated to reflux for an additional 24 hours. At three successive 24 hour intervals, 1.0 mmol additional DDQ was added and heating continued until no starting material was left. The reaction was cooled to room temperature at which time most of the hydroquinone by-product precipitated. The reaction was filtered and concentrated. The residue was chromatographed on silica gel eluting with 50% ethyl acetate in hexane to yield 4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide (352 mg, 90%): 1H NMR (acetone d6) δ=6.89 (broad s, 2H), 7.5 (m, 1H), 7.7 (m, 2H), 7.89 (s, 2H), 8.0 (d, 2H, j=8.7 Hz), 8.15 (d, 1H, j=8.3 Hz), 8.3 (d, 2H, j=8.7 Hz); 19F NMR (acetone d6) δ-61.7 ppm (s, 3F).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperaturethe reaction was heated
  4. temperatureto reflux for an additional 24 hours
  5. temperatureheating
  6. waitwas left
  7. customprecipitated
  8. filtrationThe reaction was filtered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel eluting with 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-88adc217610d497b84c9c2350ff3dd8c
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05696143

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