2,4,6-Trifluoroaniline → HCID 178471959, Verbindung

HRID 1415916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1415916
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].[Cl:11][C:12]1[N:29]=[C:28]([Cl:30])[C:27]([F:31])=[CH:26][C:13]=1[C:14]([C:16](=[CH:22]OCC)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15]>C1(C)C=CC=CC=1>[Cl:11][C:12]1[N:29]=[C:28]([Cl:30])[C:27]([F:31])=[CH:26][C:13]=1[C:14]([C:16](=[CH:22][NH:4][C:3]1[C:2]([F:1])=[CH:8][C:7]([F:9])=[CH:6][C:5]=1[F:10])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15]

Komponenten

4

Edukt 2

HCID 677652,4,6-TrifluoroanilineHCID 54342804Ethyl 2-(2,6-dichloro-5-fluoronicotinoyl)-3-ethoxyacrylate

Produkt 1

HCID 178471959HCID 178471959, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

With ice cooling, 5 ml of a toluene solution containing 1.39 ml of 2,4,6-trifluoroaniline was added dropwise to 10 ml of a toluene solution containing 6.40 g of ethyl 2-(2,6-dichloro-5-fluoronicotinoyl)-3-ethoxyacrylate and stirred overnight at room temperature. The solvent was distilled off then to the residue, ethanol was added. The resulting crystals were collected by filtration and washed with diethyl ether, to give ethyl 2,6-dichloro-5-fluoronicotinoyl-3-(2,4,6-trifluorophenyl)aminoacrylate. To 9 ml of a N,N-dimethylformamide solution containing 2.0 g of ethyl 2,6-dichloro-5-fluoronicotinoyl-3-(2,4,6-trifluorophenylamino)acrylate was added 0.63 g of potassium carbonate. The solution was stirred for 90 minutes at room temperature. The reaction solution was poured into ice water, the precipitated solid was collected by filtration and washed with ethanol and diethyl ether, to give 1.38 g of the title compound.

Aufarbeitung

  1. distillationThe solvent was distilled off
  2. additionto the residue, ethanol was added
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-35a21c4dc7d245d38cfbfecafcad9e0f
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05910498

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