1,2-Dibromoethane → ethyl 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate

HRID 2295732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295732
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([SH:12])[NH:9]2)=[CH:4][C:3]=1[F:19].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH2:27]Br>CN(C)C=O>[CH2:16]([O:15][C:13]([C:7]1[C:6](=[O:18])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([F:19])[CH:4]=2)[N:9]2[CH2:26][CH2:27][S:12][C:8]=12)=[O:14])[CH3:17]

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178470137HCID 178470137, Verbindung

Produkt 1

HCID 10404195ethyl 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Three grams (0.01 mol) of ethyl 7-chloro-6-fluoro-2-mercapto-4-oxo-1,4-dihydroquinoline-3-carboxylate was dissolved in 10 ml of dimethyl formamide, then 4.1 grams (0.03 mol) of anhydrous potassium carbonate was added thereto and, with stirring at a room temperature, 1.9 grams (0.01 mol) of ethylene dibromide was dropped thereinto. The mixture was stirred at a room temperature overnight. The content was concentrated under reduced pressure and water was added to the residue. Crystals separated out therefrom were collected by filtration immediately, washed with water, dried and the crystals were recrystallized from ethanol to give the title compound. Colorless crystals. Yield 3.5 grams (94 percent). All of melting point, elementary analysis data, infrared absorption spectra, and nuclear magnetic resonance spectra coincided with those in example 15.

Aufarbeitung

  1. stirringThe mixture was stirred at a room temperature overnight
  2. concentrationThe content was concentrated under reduced pressure and water
  3. additionwas added to the residue
  4. customCrystals separated out
  5. filtrationtherefrom were collected by filtration immediately
  6. washwashed with water
  7. customdried
  8. customthe crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5fef51a86c8b49efa64a32eb598a08dd
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04426381

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