Carbon Tetrachloride → HCID 86658928, Verbindung

HRID 68167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68167
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:21].C1COCC1.[F:30][C:31]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH3:44])=[C:37]2[C:32]=1[C:33](=[O:53])[C:34]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)=[CH:35][NH:36]2.[C:54]([CH:57](O)[CH2:58][NH-:59])([OH:56])=[O:55]>O>[F:30][C:31]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH3:44])=[C:37]2[C:32]=1[C:33](=[O:53])[C:34]([C:45]1[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=1)=[CH:35][NH:36]2.[C:54]([CH:57]([Cl:21])[CH2:58][NH-:59])([OH:56])=[O:55]

Komponenten

6

Edukt 4

HCID 5943Carbon TetrachlorideHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86658929HCID 86658929, Verbindung

Produkt 1

HCID 86658928HCID 86658928, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Triphenyl phosphine (2.47 g, 9.8 mmol) and carbon tetrachloride (1.4 g, 9.1 mmol) were added to a THF solution (30 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline-2-carboxy-(2-hydroxyethyl)amide (3.0 g, 7.24 mmol) and heated under reflux for 2 hours. The mixture was cooled to room temperature, and water was then added thereto, followed by extraction with dichloromethane. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=100:0→20:1). The purified material was concentrated to dryness under reduced pressure, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxy-(2-chloroethyl)amide (1.8 g, yield: 58%).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. extractionfollowed by extraction with dichloromethane
  4. washThe thus-obtained organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. concentrationThe purified material was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-70f76ad6b44b4f4ea6524a0d4bf013ad
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045108E1

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