Aniline → N-Phenylmaleimide

HRID 262421Notes

Reaction equation

HRID 262421 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 13662N-Phenylmaleimide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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.)

Sources & evidence

ORD record
ord-70da2d85e5dc485d8ae20fa76713538f
Source dataset
uspto-grants-1979_05
Patent number
US04154737

Reaction notes

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