Citraconic Anhydrides → HCID 54131587, compound

HRID 1194664Notes

Reaction equation

HRID 1194664 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:17][C:18]1[C:19]([O:21][C:22](=[O:24])[CH:23]=1)=[O:20]>C(=S)=S>[O:16]=[C:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:19](=[O:20])[C:18]([CH3:17])=[CH:23][C:22]([OH:24])=[O:21]

Participants

5

Reactant 3

HCID 12012Citraconic AnhydridesHCID 783751-Phenylpyrrolidin-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54131587HCID 54131587, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

66.7 g (0.5 mole) of anhydrous aluminum chloride are suspended in 150 ml of carbon disulphide. 32.2 g (0.2 mole) of N-phenyl-pyrrolidin-2-one and 22.4 g (0.2 mole) of methylmaleic anhydride are added, while stirring and cooling. The mixture is heated under reflux until a viscous mass is formed, and this is left to stand at room temperature for 40 hours, the solvent is decanted off and the mixture is decomposed carefully with icewater and concentrated aqueous hydrochloric acid and extracted with methylene cchloride or ethyl acetate. The organic phase is extracted with dilute sodium hydroxide solution, the aqueous phase is clarified by filtration, acidified with acetic acid and extracted and the extract is concentrated. The resulting oil is further reacted directly.

Workup

  1. temperaturecooling
  2. temperatureThe mixture is heated
  3. temperatureunder reflux until a viscous mass
  4. customis formed
  5. waitthis is left
  6. customthe solvent is decanted off
  7. extractionextracted with methylene cchloride or ethyl acetate
  8. extractionThe organic phase is extracted with dilute sodium hydroxide solution
  9. filtrationthe aqueous phase is clarified by filtration
  10. extractionextracted
  11. concentrationthe extract is concentrated
  12. customThe resulting oil is further reacted directly

Sources & evidence

ORD record
ord-5d2fb6b8ca1046f4822aa4f0e0d23dbb
Source dataset
uspto-grants-1989_03
Patent number
US04816454

Reaction notes

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