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

HRID 478047

反応式

HRID 478047 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62601Nickel acetate tetrahydrate触媒HCID 962Water溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-c7149af7e208494380914fed1a944b35
出典データセット
uspto-grants-1989_12
特許番号
US04889912

関連ノート

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