Carbon Dioxide → 3-(4-Methylphenyl)-1H-pyrrole-2,5-dione

HRID 371126Notes

Reaction equation

HRID 371126 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[C:13]1(=[O:19])[NH:17][C:16](=[O:18])[CH:15]=[CH:14]1.C(=O)=O.C([O-])(=O)C.[Na+]>Cl.O.CC(C)=O>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([C:14]2[C:13]([NH:17][C:16](=[O:18])[CH:15]=2)=[O:19])=[CH:3][CH:4]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 7813p-ToluidineHCID 10935MaleimideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 219243273-(4-Methylphenyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A 53.6 g portion of p-toluidine was dissolved in a mixture of 150 ml of 12N-hydrochloric acid and 100 ml of water, cooled in an ice-salt bath. A 100 g portion of ice was added and then a solution of 35 g of sodium nitrite in 80 ml of water was added dropwise with stirring over 1/2 hour. A solution of 48.5 g of maleimide in 400 ml of acetone was then added in one portion and the mixture was cooled in an ice-salt bath with 20 g of dry ice added to the reaction mixture. A 125 g portion of sodium acetate was added to achieve pH 3. Ten minutes later 5.0 g of cupric chloride dihydrate was added. The mixture was filtered and the filtrate was allowed to stand 64 hours. The solid was collected, added to 30 ml of 2,6-lutidine and heated on a steam bath for 1/2 hour, then poured into one liter of water and filtered. The filtrate produced pale yellow crystals which were collected, giving 2-(p-tolyl)maleimide.

Workup

  1. temperaturecooled in an ice-salt bath
  2. additionA 100 g portion of ice was added
  3. additionadded to the reaction mixture
  4. filtrationThe mixture was filtered
  5. waitto stand 64 hours
  6. customThe solid was collected
  7. additionadded to 30 ml of 2,6-lutidine
  8. temperatureheated on a steam bath for 1/2 hour
  9. additionpoured into one liter of water
  10. filtrationfiltered
  11. customThe filtrate produced pale yellow crystals which
  12. customwere collected

Sources & evidence

ORD record
ord-f92d0a873d004815879105c9bfbae7ac
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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