Phthalimide → N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

HRID 5861

Reaktionsgleichung

Reaktionsgleichung von HRID 5861
Br[CH:2]=[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH2:4]1.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:23]2[C:22](=[O:24])[C:21]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]3[C:19]2=[O:29])=[CH:4][CH:5]=1)([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 54201998Methyl 2-[4-(bromomethylene)phenyl]benzoate

Produkt 1

HCID 19794415N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Methyl 2-[4-(bromomethylene)phenyl]benzoate (1.22 g, 0.04 mole), phthalimide (0.59 g, 0.04 mole), and potassium carbonate (0.55 g, 0.04 mole) are combined in 120 mL acetonitrile. The mixture is heated at reflux for 24 hours. At that time the mixture is filtered through celite and rotovapped to a residue. The residue is crystallized from ethyl acetate to afford 1.1 g (71%) of the title compound as a tan solid mp 148°-150° C. 1H NMR (CDCl3) 7.9-7.1 (12H, m); 4.92 (2H, s); 3.63 (3H, s). Mass Spec. (DCl) m/z 372 (M+H). Analysis--calc'd for C23H17NO4.1/2 H2O: C, 72.62; H, 4.77: N, 3.68; found: C, 72.88; H, 4.55; N, 3.77.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. filtrationAt that time the mixture is filtered through celite
  4. customThe residue is crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-588df9429c01452987b98d1b2b5b1d86
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246940

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