4-Hydrazinylbenzenesulfonamide hydrochloride → 4,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

HRID 1939309

Reaktionsgleichung

Reaktionsgleichung von HRID 1939309
[F:1][C:2]([F:17])([F:16])[C:3](=[C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=O)O.[CH:18]1[C:23]([NH:24][NH2:25])=[CH:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=1.Cl>C(O)C>[F:1][C:2]([F:17])([F:16])[C:3]1[C:5]2[C:6](=[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]3=[CH:13][CH:14]=2)[N:24]([CH:23]2[CH2:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=[CH:18]2)[N:25]=1

Komponenten

4

Edukt 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 178516600HCID 178516600, Verbindung

Produkt 1

HCID 189203554,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamideAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A 100 mL one neck round bottomed flask equipped with reflux condenser, nitrogen inlet and provisions for magnetic stirring was charged with 3,4-dihydro-2-[2,2,2-trifluoro-1-hydroxyethylidene]-1(2H)-naphthalenone from Step 1 (1.21 g, 5.0 mmol), 4-sulfonamidophenylhydrazine hydrochloride (1.12 g, 5.0 mmol) and 25 mL of absolute ethanol. The solution was warmed to reflux for 15 hours, cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water and with brine, dried over anhydrous MgSO4, filtered and reconcentrated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isooctane to give 1.4 g (71%) of pure 4,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide: mp 257°-258° C.; 1H NMR (CDCl3 /CD3OD, 4:1) δ 2.7 (m, 2H), 2.9 (m, 2H), 6.6 (m, 1H), 6.9 (m, 1H), 7.1 (m, 1H), 7.16 (m, 1H), 7.53 (m, 2H), 7.92 (m, 2H); 19F NMR CDCl3 δ-62.5. FAB-MS M+H=394.

Aufarbeitung

  1. temperaturewith reflux condenser, nitrogen inlet
  2. temperatureThe solution was warmed
  3. temperatureto reflux for 15 hours
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water and with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. customThe residue was recrystallized from a mixture of ethyl acetate and isooctane

Quellen und Nachweise

ORD-Eintrag
ord-e031a472bc5a4e3d9433214f3c7c1bae
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05696143

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