N,N-Diethylaniline → 1,1,2-Ethenetricarbonitrile, 2-(4-(diethylamino)phenyl)-

HRID 356226

Reaktionsgleichung

Reaktionsgleichung von HRID 356226
[CH2:1]([N:3]([CH2:10][CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[C:12]([C:14]([C:20]#[N:21])=[C:15](C#N)[C:16]#[N:17])#[N:13].CCCCCC>CN(C=O)C.C(=O)([O-])O.[Na+]>[CH2:10]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:15]([C:16]#[N:17])=[C:14]([C:20]#[N:21])[C:12]#[N:13])=[CH:6][CH:5]=1)[CH3:11]

Komponenten

6

Edukt 3

HCID 7061N,N-DiethylanilineHCID 8058HexaneHCID 12635Tetracyanoethylene

Produkt 1

HCID 906081,1,2-Ethenetricarbonitrile, 2-(4-(diethylamino)phenyl)-Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In an atmosphere of argon, 42.3 g (0.28 mol) of N,N-diethylaniline was dissolved in 570 ml of anhydrous DMF, and the solution obtained was cooled to 0° C., and then 46.3 g (1.25-fold equivalent weight) of tetracyanoethylene was added thereto. Then, the solution obtained was restored to room temperature, and stirred for 4.5 hours, which was thereafter poured in 1 liter of a saturated aqueous sodium hydrogencarbonate solution. The solid thus deposited was filtered to obtain a residue, and the residue was subjected to azeotropic distillation twice with 300 ml of toluene to remove the water content. Thereafter, 300 ml of ethyl acetate was added, and the atmosphere was replaced with argon, followed by heating at 80° C. for 1 hour to effect dissolution. To the mixture obtained, 800 ml of hexane was added with stirring, and the solution obtained was cooled to room temperature. The solid thus deposited was collected by filtration, and the residue obtained was vacuum-dried to obtain 51.7 g of N,N-diethyl-4-tricyanovinylaniline (yield: 74%).

Aufarbeitung

  1. customthe solution obtained
  2. customThen, the solution obtained
  3. customwas restored to room temperature
  4. filtrationThe solid thus deposited was filtered
  5. customto obtain a residue
  6. distillationthe residue was subjected to azeotropic distillation twice with 300 ml of toluene
  7. customto remove the water content
  8. additionThereafter, 300 ml of ethyl acetate was added
  9. temperatureby heating at 80° C. for 1 hour
  10. dissolutiondissolution
  11. customTo the mixture obtained
  12. stirringwith stirring
  13. customthe solution obtained
  14. temperaturewas cooled to room temperature
  15. filtrationThe solid thus deposited was collected by filtration
  16. customthe residue obtained
  17. customwas vacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-c823d718a0ea45b4aabb3a93f33f610c
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834575

Verknüpfte Notizen

Wird geladen…