Triethylamine → HCID 53640509, Verbindung

HRID 525963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525963
C(N(CC)CC)C.[CH3:8][N:9]([CH3:17])[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[F:18][C:19]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[CH3:8][N:9]([CH3:17])[CH:10]=[C:11]([C:21](=[O:22])[C:20]1[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:19]=1[F:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 1451642,4,5-Trifluorobenzoyl chloride

Produkt 1

HCID 53640509HCID 53640509, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of triethylamine (107 mL, 771 mmol) and ethyl 3-(dimethylamino)acrylate (55.2 mL, 386 mmol) in toluene (250 mL) was added dropwise a toluene solution of 2,4,5-trifluorobenzoyl chloride (50 g, 257 mmol). The mixture was stirred at 90° C. for 3 h. LCMS showed completion of reaction. After cooling down, the reaction mixture was washed with water and extracted with EA. The organic layer was dried over Na2SO4, filtered and concentrated to afford ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate (65 g, 216 mmol, 84% yield) as a brown oil. LCMS: (M+H)+: 302.1.

Aufarbeitung

  1. customcompletion of reaction
  2. temperatureAfter cooling down
  3. washthe reaction mixture was washed with water
  4. extractionextracted with EA
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-277f1a04a18a47f4a738b7db5e372231
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340556B2

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