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

HRID 1721117

Reaktionsgleichung

Reaktionsgleichung von HRID 1721117
[F:1][C:2]([F:17])([F:16])[C:3]([CH: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 69171222-Trifluoroacetyl-1-tetralone

Produkt 1

HCID 189203554,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A 100 mL one necked round bottomed flask equipped with reflux condenser, nitrogen inlet and provisions for magnetic stirring was charged with 2-trifluoroacetyl-1-tetralone (1.21 g, 5.0 mmol), 4-sulfonamido phenylhydrazine hydrochloride (1.12 g, 5.0 mmol) and 25 mL of absolute ethanol. The solution was then warmed to reflux for 15 h and then concentrated in vacuo. The residue was dissolved in ethyl acetate and then washed with water, brine, dried over anhyd. MgSO4, filtered and concentrated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isooctane to give g, 71% of pure produce with mp 257°-258° C. 1H NMR (CDCl3 /CD3OD, 4:1) δ2.7 (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); 19 F NMR CDCl3 δ-62.5. FAB-MS M+H=394.

Aufarbeitung

  1. temperaturewith reflux condenser, nitrogen inlet
  2. temperatureThe solution was then warmed
  3. temperatureto reflux for 15 h
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water, brine
  7. customdried over anhyd
  8. filtrationMgSO4, filtered
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from a mixture of ethyl acetate and isooctane
  11. customto give g, 71%
  12. customof pure produce with mp 257°-258° C

Quellen und Nachweise

ORD-Eintrag
ord-a40c7524c3604558a8e2b15e574ed849
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05508426

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