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Potassium Carbonate → Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylate

HRID 72748
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 72748
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[CH2:15]([O:17][C:18](/[CH:20]=[CH:21]/[C:22]1[NH:26][C:25]([C:27](OCC)=[O:28])=[CH:24][CH:23]=1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)(=O)C.O.C(OCC)C.CS(C)=O>[O:28]=[C:27]1[NH:12][C:3]2[C:2](=[CH:7][CH:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:4]=2)[N:26]2[C:22](/[CH:21]=[CH:20]/[C:18]([O:17][CH2:15][CH3:16])=[O:19])=[CH:23][CH:24]=[C:25]12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 53836411H-Pyrrole-2-carboxylic acid, 5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-, ethyl ester

Produkt 1

HCID 59198853Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylateAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-fluoro-2-nitro-4-trifluoromethylbenzene 523 mg, ethyl 5-[(E)-2-ethoxycarbonylvinyl]-1H-pyrrole-2-carboxyate 593 mg, potassium carbonate 864 mg and dimethylsulfoxide 10 mL was heated at 100° C. for 3.5 hours. After cooling off the reaction liquid, 100 mL of diethyl ether was added, followed by filtration. To the filtrate 100 mL of water was added to separate the organic layer. The aqueous layer was extracted twice with 50 mL of diethyl ether, and the extract was combined with the organic layer, followed by washing three times with 20 mL of water and once with 20 mL of saturated brine by the order stated. After drying the same over magnesium sulfate, the solvent was distilled off under reduced pressure, leaving 965 mg of a brown, viscous substance. This was dissolved in a liquid mixture of 12 mL of acetic acid and 5 mL of water, and to the solution 1.31 g of sodium hyposulfite was added, followed by heating under reflux for 30 minutes. After cooling off the reaction liquid, 50 mL of water was added and the precipitated crystals were recovered by filtration. The crystals were washed with water and diethyl ether, and dried under heating to provide 600 mg of the title compound.

Aufarbeitung

  1. temperatureAfter cooling off
  2. additionwas added
  3. filtrationfollowed by filtration
  4. additionTo the filtrate 100 mL of water was added
  5. customto separate the organic layer
  6. extractionThe aqueous layer was extracted twice with 50 mL of diethyl ether
  7. washby washing three times with 20 mL of water
  8. dry with materialAfter drying the same over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customleaving 965 mg of a brown, viscous substance
  11. temperatureby heating
  12. temperatureunder reflux for 30 minutes
  13. temperatureAfter cooling off
  14. additionwas added
  15. filtrationthe precipitated crystals were recovered by filtration
  16. washThe crystals were washed with water and diethyl ether
  17. customdried
  18. temperatureunder heating

Quellen und Nachweise

ORD-Eintrag
ord-c6ea9addc70d4c48927dfb8cf460b5e3
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829000B2

Notizen zur Reaktion

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