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

HRID 1646921

Reaktionsgleichung

Reaktionsgleichung von HRID 1646921
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. (DCI) 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-081acad0019a4f4080f0a0f1b1cba614
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182288

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