Urea → HCID 10640444, compound

HRID 1872747Notes

Reaction equation

HRID 1872747 reaction equation
[C:1]1([CH:7]([C:14]([OH:16])=O)[CH2:8][C@@H:9]([C:11]([OH:13])=O)[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[NH2:28]C(N)=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1.C(O)C>[C:1]1([CH:7]2[C:14](=[O:16])[NH:28][C:11](=[O:13])[CH:9]([N:10]3[C:20](=[O:21])[C:19]4[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]3=[O:22])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1176UreaHCID 6811Phthalic AnhydrideHCID 7918Acetic AnhydrideHCID 21140795HCID 21140795, compound

Product 1

HCID 10640444HCID 10640444, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

3.00 g (12 mmoles) 4-phenylglutamic acid and 2.12 g (14 mmoles) phthalic anhydride were heated for 6 hours under reflux in 40 ml of dry pyridine. After removing the solvent by distillation, the residue was taken up in 50 ml of 5% HCl and extracted with ethyl acetate. The organic phase was washed with water, decolourised with activated carbon and dried over sodium sulphate. After removing the solvent by distillation, the residue was heated under reflux for 1 hour in 40 ml acetic anhydride. The solution was subsequently concentrated and treated with ether. The precipitate formed was filtered off under suction and was recrystallised from dry toluene. 2.00 g (6 mmoles) of the crystalline material and 0.19 g (3 mmoles) urea were fused on an oil bath at about 200° C. for 30 minutes. The solidified melt was heated briefly to boiling, with 4 ml acetic anhydride and 8 ml ethanol in succession. The precipitated solid was recrystallised from DMF/water. 0.80 g (40% theoretical) 2-(5-phenyl-2,6-dioxo-piperidin-3-yl)-1,3-dihydro-2H-isoindole-1,3-dione (2) were obtained, with a melting point of 228 to 231° C.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. customAfter removing the solvent
  7. distillationby distillation
  8. temperaturethe residue was heated
  9. temperatureunder reflux for 1 hour in 40 ml acetic anhydride
  10. concentrationThe solution was subsequently concentrated
  11. additiontreated with ether
  12. customThe precipitate formed
  13. filtrationwas filtered off under suction
  14. customwas recrystallised from dry toluene
  15. temperatureThe solidified melt was heated briefly
  16. customThe precipitated solid was recrystallised from DMF/water

Sources & evidence

ORD record
ord-448d1c0f52e94809a6ac31e87bec31f5
Source dataset
uspto-grants-2000_08
Patent number
US06110941

Reaction notes

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