Acetic Anhydride → 1H-Pyrrole-2,5-dione, 1-(3-ethynylphenyl)-

HRID 478047

반응식

HRID 478047 반응식
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([C:15]#[CH:16])[CH:12]=[CH:13][CH:14]=1.C(OC(=O)C)(=O)C>O.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[C:15]([C:11]1[CH:10]=[C:9]([N:8]2[C:4](=[O:5])[CH:3]=[CH:2][C:1]2=[O:7])[CH:14]=[CH:13][CH:12]=1)#[CH:16]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 104682Benzenamine, 3-ethynyl-

생성물 1

HCID 7100601H-Pyrrole-2,5-dione, 1-(3-ethynylphenyl)-수율 80.1%

시약·촉매·용매 2

HCID 62601Nickel acetate tetrahydrate촉매HCID 962Water용매

실험 절차

Maleic anhydride (79.6 g, 0.81 mole) was added to a solution of distilled 3-aminophenylacetylene (95.1 g, 0.81 mole) dissolved in 500 mL of dry N,N'-dimethylacetamide (DMAc) at 5°-10° C. After addition, another 300 mL of DMAc was added and the mixture stirred at room temperature for two hours. Nickel acetate tetrahydrate (0.8 g) and acetic anhydride (300 mL) were added to the reaction mixture and stirring was continued for 12 hours at room temperature to affect cyclodehydration. The crude product was isolated by precipitation in water and recrystallized from methanol to provide N-(3-ethynylphenyl)maleimide (128 g, 80% yield) as a yellow crystalline solid, mp 129°-131° C. Elemental analysis calculated for C12H7NO2 : C, 73.09%; H, 3.58%; N, 7.10%. Found: C, 72.94%; H, 3.61%; N, 7.04%.

후처리

  1. additionAfter addition
  2. stirringstirring
  3. waitwas continued for 12 hours at room temperature
  4. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-c7149af7e208494380914fed1a944b35
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889912

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