Maleic Anhydride → 1H-Pyrrole-2,5-dione, 1-(2,4,6-tribromophenyl)-

HRID 247164Notes

Reaction equation

HRID 247164 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[C:5]([Br:10])[C:3]=1[NH2:4].[C:11]1(=O)[O:16][C:14](=[O:15])[CH:13]=[CH:12]1.[Sn](Cl)Cl>>[Br:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[C:5]([Br:10])[C:3]=1[N:4]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]1=[O:16]

Participants

4

Reactant 3

HCID 7923Maleic AnhydrideHCID 89862,4,6-TribromoanilineHCID 24479Stannous Chloride

Product 1

HCID 30171561H-Pyrrole-2,5-dione, 1-(2,4,6-tribromophenyl)-

Conditions

Temperature
142 °C

Procedure

A mixture of 2,4,6-tribromoaniline (1.20g, 3.64 mmol), maleic anhydride (0.83g, 8.5 mmol) and tin(II) chloride (0.064g, 0.34 mmol) is heated to 142° C. with mixing and held at this temperature for 1.9 hours. The reaction mixture is cooled, extracted with xylene, filtered and the resulting filtrate water washed. Solvent removal yielded N-(2,4,6-tribromophenyl)maleimide. Analysis by High Pressure Liquid Chromatography (HPLC) showed conversion of 2,4,6-tribromoaniline to be 99.9% and selectivity to N-(2,4,6-tribromophenyl)maleimide based on reacted 2,4,6-tribromoaniline of 75.0%.

Workup

  1. additionwith mixing
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with xylene
  4. filtrationfiltered
  5. washthe resulting filtrate water washed
  6. customSolvent removal

Sources & evidence

ORD record
ord-18dd8ed719df4f0388642cdc678801c0
Source dataset
uspto-grants-1987_11
Patent number
US04705866

Reaction notes

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