Sodium Acetate → N-(3-Iodophenyl)maleimide

HRID 982158노트

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HRID 982158 반응식
[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

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 2266804HCID 2266804, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
120 °C

실험 절차

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 ).

후처리

  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

출처 및 근거

ORD 기록
ord-2fe72997ab6b4ef2837e3238e51af00a
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994557

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