2-(7-Chloroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine → 11-Acetylthio-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

HRID 232882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232882
[C:1]([OH:4])(=[S:3])[CH3:2].[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH2:16][O:17][C:18]3[CH:33]=[CH:32][C:21]4[O:22][CH2:23][C:24]5[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=5[CH:26](O)[C:20]=4[CH:19]=3)=[N:13]2)=[CH:8][CH:7]=1>FC(F)(F)C(O)=O.C(Cl)Cl>[C:1]([S:3][CH:26]1[C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[CH2:23][O:22][C:21]2[CH:32]=[CH:33][C:18]([O:17][CH2:16][C:12]3[CH:11]=[CH:10][C:9]4[C:14](=[CH:15][C:6]([Cl:5])=[CH:7][CH:8]=4)[N:13]=3)=[CH:19][C:20]1=2)(=[O:4])[CH3:2]

Komponenten

5

Edukt 2

HCID 233591192-(7-Chloroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepineHCID 178418634HCID 178418634, Verbindung

Produkt 1

HCID 2335910911-Acetylthio-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Under ice cooling and stirring, 1.25 ml of thioacetic acid was added to 7.03 g of 2-(7-chloroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 36 dissolved in a mixed solution of 58 ml of trifluoroacetic acid and 30 ml of methylene chloride and the mixture was stirred at the same temperature for 3 hours. 300 ml of ice water was added to the reaction mixture, crystals precipitated by neutralization with a 1N-sodium hydroxide aqueous solution were collected by filtration and these crystals were dissolved in methylene chloride. Then, this organic layer was washed with water and dried over anhydrous sodium sulfate and then the solvent was removed. The resulting residue was applied to silica gel column chromatography to obtain 4.6 g of the title compound as white powder.

Aufarbeitung

  1. customobtained in Reference example 36
  2. stirringthe mixture was stirred at the same temperature for 3 hours
  3. customprecipitated by neutralization with a 1N-sodium hydroxide aqueous solution
  4. filtrationwere collected by filtration
  5. dissolutionthese crystals were dissolved in methylene chloride
  6. washThen, this organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-ea0efdb443bb4e00b7b8dab403aac603
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591752

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