4-Cyanobenzaldehyde → (E)-4-[3-Acetyl-1-(3,5-dichlorophenyl)-2,5-dioxoimidazolidin-4-ylidenemethyl]benzonitrile

HRID 1792859

Reaktionsgleichung

Reaktionsgleichung von HRID 1792859
C(O[C:6]([N:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[C:9]1=[O:22])=[O:7])(C)(C)C.[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)#[N:24].[CH3:33]C([O-])=O.[Na+]>CC(OC(C)=O)=O>[C:6]([N:8]1[C:9](=[O:22])[N:10]([C:14]2[CH:15]=[C:16]([Cl:21])[CH:17]=[C:18]([Cl:20])[CH:19]=2)[C:11](=[O:13])/[C:12]/1=[CH:29]\[C:28]1[CH:31]=[CH:32][C:25]([C:23]#[N:24])=[CH:26][CH:27]=1)(=[O:7])[CH3:33]

Komponenten

5

Edukt 3

HCID 660424-CyanobenzaldehydeHCID 517045Sodium AcetateHCID 235885583-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 10111572(E)-4-[3-Acetyl-1-(3,5-dichlorophenyl)-2,5-dioxoimidazolidin-4-ylidenemethyl]benzonitrileAusbeute 109,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A mixture of 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxylic acid tert-butyl ester (3.45 g, 10 mmol) (Preparation 11), 4-cyanobenzaldehyde (1.31 g, 10 mmol) and NaOAc (0.82 g, 10 mmol) was refluxed for 3 h in Ac2O (50 ml). The solid obtained after concentration was taken into a mixture of ice/water and DCM. The organic layer was dried and concentrated to yield a solid (4.4 g) which was chromatographed over silica gel (eluent: DCM) to yield 4-[3-acetyl-1-(3,5-dichlorophenyl)-2,5-dioxoimidazolidin-4-ylidenemethyl]-benzonitrile as a white solid (1.25 g). mp=212° C. 1H NMR (CDCl3): 8.52 (1H, s), 7.6–7.75 (4H, m), 7.43 (1H, m), 7.37 (2H, m), 2.78 (3H, s).

Aufarbeitung

  1. customThe solid obtained
  2. concentrationafter concentration
  3. additionwas taken into a mixture of ice/water and DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c24b3f2993e946fcbda0dfb1310bbbb5
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078420B2

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