Triethylamine → HCID 76759590, Verbindung

HRID 444704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444704
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8](=O)[CH:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O=P(Cl)(Cl)[Cl:20].CCN(CC)CC>C(Cl)(Cl)Cl>[Cl:20][C:8]([C:3]1[S:4][CH:5]=[C:6]([CH3:7])[C:2]=1[Cl:1])=[C:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 67115664HCID 67115664, Verbindung

Produkt 1

HCID 76759590HCID 76759590, VerbindungAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of ethyl 3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-oxopropanoate (15.40 g, 56.67 mmol, 1 eq.) in 200 ml of CHCl3 was added POCl3 (86.9 g, 566 mmol, 10 eq.). Et3N (14.33 g, 141.6 mmol, 2.5 eq.) was added dropwise with stirring at 5° C., and the mixture was refluxed for 4 h. The mixture was evaporated. After evaporation, the mixture was diluted with DCM (CH2Cl2) and with ice water and was extracted with DCM (CH2Cl2) and washed with brine. The organic layers were combined and dried over MgSO4 before concentration under reduced pressure. The residue was subjected to column chromatography on silica gel to give ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (11 g, 66% yield) as a mixture of 2 isomers

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 h
  2. customThe mixture was evaporated
  3. customAfter evaporation
  4. additionthe mixture was diluted with DCM (CH2Cl2) and with ice water
  5. extractionwas extracted with DCM (CH2Cl2)
  6. washwashed with brine
  7. dry with materialdried over MgSO4 before concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4847b81d5f864422aa202a73eb9b298b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476197B2

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