Aniline → N-Phenylmaleimide

HRID 262421

Reaktionsgleichung

Reaktionsgleichung von HRID 262421
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(OC(=O)C)(=O)C>O.CC(C)=O.C(N(CC)CC)C>[C:9]1([N:8]2[C:4](=[O:5])[CH:3]=[CH:2][C:1]2=[O:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

8

Edukt 4

HCID 6115AnilineHCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 24644Magnesium chloride hexahydrate

Produkt 1

HCID 13662N-Phenylmaleimide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A reaction flask was equipped as in Example 1. To a solution of maleic anhydride (1.12 parts) in 5.6 parts acetone was added a solution of 1 part aniline, 0.375 part triethylamine, and 1.9 parts acetone over a 30-minute period. The resulting heterogeneous mixture was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.093 part) and 1.4 parts acetic anhydride were added all at once. The temperature was raised to 50° C. for 3 hours. The homogeneous mixture was cooled and 14 parts water added. The precipitated product was isolated by vacuum filtration, washed with water, and air dried. The crude product was recrystallized from ethanol/water (90/10 vol.) to yield 0.89 part N-phenyl maleimide, m.p. 84°-86° C.

Aufarbeitung

  1. customA reaction flask was equipped as in Example 1
  2. temperatureThe temperature was raised to 50° C. for 3 hours
  3. temperatureThe homogeneous mixture was cooled
  4. customThe precipitated product was isolated by vacuum filtration
  5. washwashed with water, and air
  6. customdried
  7. customThe crude product was recrystallized from ethanol/water (90/10 vol.)

Quellen und Nachweise

ORD-Eintrag
ord-70da2d85e5dc485d8ae20fa76713538f
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154737

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