Phosphoric Acid → N-Phenylmaleimide

HRID 1731896Notes

Reaction equation

HRID 1731896 reaction equation
[C:1]1([NH:7][C:8](=[O:14])/[CH:9]=[CH:10]\[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(=O)(O)(O)O>>[C:1]1([N:7]2[C:8](=[O:14])[CH:9]=[CH:10][C:11]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 1550938Maleic acid anilide

Product 1

HCID 13662N-Phenylmaleimide

Conditions

Temperature
210 °C

Procedure

The slurry containing the N-phenyl maleinamic acid and 10 g of ortho-phosphoric acid added thereto were heated at 210° C. for three hours. The resultant reaction mixture was cooled to 30° C., washed with water, and distilled under a vacuum to expel tetrahydronaphthalene and obtain 78 g of N-phenyl maleimide crystals. By liquid chromatography, the crystals were found to have purity of 87.3% by weight, indicating the yield thereof to be 73.2 mol%.

Workup

  1. additionadded
  2. customThe resultant reaction mixture
  3. temperaturewas cooled to 30° C.
  4. washwashed with water
  5. distillationdistilled under a vacuum

Sources & evidence

ORD record
ord-73499e678beb421eb5e788c078d6f10f
Source dataset
uspto-grants-1986_11
Patent number
US04623734

Reaction notes

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