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Trifluoroacetic acid → HCID 178470134, Verbindung

HRID 1722072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1722072
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([S:15]CC2C=CC(OC)=CC=2)[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.C1(OC)C=CC=CC=1>>[OH:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([SH:15])[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 178470096HCID 178470096, Verbindung

Produkt 1

HCID 178470134HCID 178470134, VerbindungAusbeute 76,9 %

Versuchsvorschrift

Ethyl 4-hydroxy-6,7,8-trifluoro-2-(p-methoxybenzylthio)quinoline-3-carboxylate (59.9 g) was added to a mixture of trifluoroacetic acid (500 g), trifluoromethanesulfonic acid (100 g) and anisole (92.5 g) at -23° to -20° C. with stirring over a period of 15 minutes. The mixture was stirred at -20° to -15° C. for 30 minutes and then at room temperature for 1.5 hour. After the reaction mixture was concentrated under reduced pressure, a piece of ice was added to the concentrate and the mixture was made alkaline with 10% aqueous sodium hydroxide. After insoluble materials were removed by filtration, the filtrate was washed with ether and made strongly acidic with concd. hydrochloric acid. The resulting powder was filtered to give the title compound (33 g), which was recrystallized from ethanol to give yellow crystals, m.p. 190° C. (dec.).

Aufarbeitung

  1. stirringThe mixture was stirred at -20° to -15° C. for 30 minutes
  2. waitat room temperature for 1.5 hour
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. additiona piece of ice was added to the
  5. concentrationconcentrate
  6. customAfter insoluble materials were removed by filtration
  7. washthe filtrate was washed with ether
  8. filtrationThe resulting powder was filtered

Quellen und Nachweise

ORD-Eintrag
ord-ffa11bc1976c4e4da69c0d2c747e0fef
Quelldatensatz
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04853469

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