Triethylamine → Ethyl 3-diethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate

HRID 255959

Reaktionsgleichung

Reaktionsgleichung von HRID 255959
[CH2:1]([N:3]([CH2:11][CH3:12])[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(N(CC)CC)C.[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[C:27]([F:31])=[CH:26][C:22]=1[C:23](Cl)=[O:24]>O1CCOCC1>[CH2:11]([N:3]([CH2:1][CH3:2])[CH:4]=[C:5]([C:23](=[O:24])[C:22]1[CH:26]=[C:27]([F:31])[C:28]([Cl:30])=[CH:29][C:21]=1[Cl:20])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:12]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 139639Ethyl 3-(diethylamino)acrylateHCID 27368212,4-Dichloro-5-fluorobenzoyl chloride

Produkt 1

HCID 54148103Ethyl 3-diethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

First 17.1 g of ethyl 3-diethylaminoacrylate are added dropwise and then 10.5 g of triethylamine are added to a solution of 22.75 g of 2,4-dichloro-5-fluorobenzoyl chloride in 80 ml of anhydrous dioxane, while cooling in ice and stirring. The mixture is stirred at room temperature for one hour, heated to boiling under reflux for 45 minutes, and the solvent is removed by distillation in vacuo, and the oily residue is taken up in methylene chloride/water. The phases are separated, and the aqueous solution is again extracted with methylene chloride. The combined organic phases are washed with water, dried with sodium sulphate, and the methylene chloride is removed in vacuo. 29 g of ethyl 3-diethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate are obtained as a brown oil.

Aufarbeitung

  1. temperaturewhile cooling in ice
  2. stirringThe mixture is stirred at room temperature for one hour
  3. temperatureheated
  4. temperatureunder reflux for 45 minutes
  5. customthe solvent is removed by distillation in vacuo
  6. customThe phases are separated
  7. extractionthe aqueous solution is again extracted with methylene chloride
  8. washThe combined organic phases are washed with water
  9. dry with materialdried with sodium sulphate
  10. customthe methylene chloride is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3d3b491826424629a8c5a2f225a8892a
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699992

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