Sodium Acetate → N-(3-Iodophenyl)maleimide

HRID 982158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 982158
[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:15])[CH:10]=[CH:11][C:12]2=[O:14])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 517045Sodium AcetateHCID 2266804HCID 2266804, Verbindung

Produkt 1

HCID 126214N-(3-Iodophenyl)maleimideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

N-(m-iodophenyl)maleamic acid (1 g, 3.15 mmol) was placed in acetic anhydride (10 mL). Sodium acetate (1 g) was added and the solution stirred at 120° C. The dark brown filtrate was evaporated to dryness under reduced pressure and the residue was dissolved in diethyl ether. The ether mixture was filtered and the filtrate was again evaporated to dryness. The residue obtained was applied to a flash chromatography column (30×200 mm) of Kieselgel 60, 230-400 mesh). Elution with ethyl acetate/hexane (1:3) (400 mL) yielded forty fractions. Fractions 25-35 were combined to provide pure pale yellow N-(m-iodophenyl)maleimide (0.75 g, 80%): TLC (EtOAc/hexane, 1:3) Rf 0.42; mp 154°-155° C.; 1H NMR (CDCl3, δ); 7.1-7.7 (multiplets, 4H, 4 aryl CH); 6.8 (singlet, 2H, 2 CHC=O ).

Aufarbeitung

  1. customThe dark brown filtrate was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in diethyl ether
  3. filtrationThe ether mixture was filtered
  4. customthe filtrate was again evaporated to dryness
  5. customThe residue obtained
  6. washElution with ethyl acetate/hexane (1:3) (400 mL)
  7. customyielded forty fractions

Quellen und Nachweise

ORD-Eintrag
ord-2fe72997ab6b4ef2837e3238e51af00a
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04994557

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