Ethyl orthoformate → HCID 69312263, Verbindung

HRID 1593771

Reaktionsgleichung

Reaktionsgleichung von HRID 1593771
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2].[CH2:17]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=1[F:27])[CH3:18].[CH2:28](OC(OCC)OCC)C>C(O)(C)C>[CH2:17]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][CH:28]=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=2[Cl:16])=[O:5])=[CH:22][C:21]=1[F:27])[CH3:18]

Komponenten

5

Edukt 3

HCID 31214Ethyl orthoformate2×HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 195992054-Ethoxy-3-fluoroaniline

Produkt 1

HCID 69312263HCID 69312263, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (5.9 g, 22.7 mmol) in 400 mL of isopropanol was added 4-ethoxy-3-fluoroaniline (3.7 g, 23.8 mmol). This mixture was heated to reflux to give a clear solution. To this solution, triethylorthoformate (11.6 mL, 69.6 mmol) was added dropwise and the reaction mixture was heated at reflux for 18 hours. Additional triethylorthoformate (11.6 mL, 69.6 mmol) was added dropwise and the reaction mixture was heated at reflux for 42 hours. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with ethyl acetate, and dried in vacuo at 40° C. to give 6.4 g (67%) of 4-ethoxy-3-fluoroanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide as a grey solid, mp 245-247° C.; MS 424.1, 426.1 (M+H)+

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. customto give a clear solution
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 18 hours
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for 42 hours
  8. filtrationthe solid was collected by filtration
  9. washwashed with ethyl acetate
  10. customdried in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-1411a352eaa849ae8ced2bb3a73ce921
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297795B2

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