Sodium Acetate → N-(3-Iodophenyl)maleimide

HRID 982158Notes

Reaction equation

HRID 982158 reaction equation
[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

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 2266804HCID 2266804, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

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 ).

Workup

  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

Sources & evidence

ORD record
ord-2fe72997ab6b4ef2837e3238e51af00a
Source dataset
uspto-grants-1991_02
Patent number
US04994557

Reaction notes

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