Maleic Anhydride → 1-(2,4,6-Trichlorophenyl)-1H-pyrrole-2,5-dione

HRID 247165Notes

Reaction equation

HRID 247165 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[C:11]1(=O)[O:16][C:14](=[O:15])[CH:13]=[CH:12]1.[Sn](Cl)Cl>>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl: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 124712,4,6-TrichloroanilineHCID 24479Stannous Chloride

Product 1

HCID 831951-(2,4,6-Trichlorophenyl)-1H-pyrrole-2,5-dione

Conditions

Temperature
140 °C

Procedure

A mixture of 2,4,6-trichloroaniline (1.20g, 6.11 mmol), maleic anhydride (0.80g, 8.2 mmol) and tin(II) chloride (0.068g, 0.36 mmol) is heated to 140° C. with mixing and held at this temperature for 2.0 hours. The reaction mixture is cooled, extracted with xylene, filtered and the resulting filtrate water washed. Solvent removal yielded N-(2,4,6-trichlorophenyl)maleimide. HPLC analysis showed conversion of 2,4,6-trichloroaniline was 96.4% and selectivity to N-(2,4,6-trichlorophenyl)maleimide based on reacted 2,4,6-trichloroaniline was 88.0%.

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-cbfe8d87d3af44f0bc14e06ff8e53803
Source dataset
uspto-grants-1987_11
Patent number
US04705866

Reaction notes

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