Oxalyl chloride → 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

HRID 1196425Notes

Reaction equation

HRID 1196425 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)(O)=[O:2].C(Cl)(=O)C([Cl:20])=O>C1C=CC=CC=1>[C:14]1(=[O:15])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([Cl:20])=[O:2])=[CH:5][CH:6]=2)[C:11](=[O:16])[CH:12]=[CH:13]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 869254-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid

Product 1

HCID 133654044-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Para-maleimidobenzoyl chloride was prepared in accordance with the procedure described by Adams et al. in J. Am. Chem. Soc., 42, 599 (1920). The N-(para-carboxyphenyl) maleimide (15 g) was suspended in about 80 ml of benzene with stirring. To this mixture was added 15 ml (a 2.5:1 molar excess) of oxalyl chloride, whereupon some gas was evolved. The mixture was then heated slowly to reflux and maintained at reflux for two hours. Excess oxalyl chloride was removed by distillation. The reaction mixture was then cooled and the yellow product recovered by suction filtration. The resultant product was washed with hexane and dried under vacuum at room temperature.

Workup

  1. additionTo this mixture was added 15 ml (a 2.5
  2. temperatureThe mixture was then heated slowly
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for two hours
  6. customExcess oxalyl chloride was removed by distillation
  7. temperatureThe reaction mixture was then cooled
  8. filtrationthe yellow product recovered by suction filtration
  9. washThe resultant product was washed with hexane
  10. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-7c4bf3296ef7466abab096e780cf337d
Source dataset
uspto-grants-1992_05
Patent number
US05114612

Reaction notes

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