Sodium Acetate → N-(3-Iodophenyl)maleimide

HRID 982158ノート

反応式

HRID 982158 の反応式
[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

参加物

4

反応物 2

HCID 517045Sodium AcetateHCID 2266804HCID 2266804、化合物

生成物 1

HCID 126214N-(3-Iodophenyl)maleimide収率 80%

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
120 °C

実験手順

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 ).

後処理

  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

出典と根拠

ORDレコード
ord-2fe72997ab6b4ef2837e3238e51af00a
出典データセット
uspto-grants-1991_02
特許番号
US04994557

反応ノート

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