Urea → HCID 10778555, compound

HRID 1872746Notes

Reaction equation

HRID 1872746 reaction equation
[CH3:1][CH:2]([C:9]([OH:11])=O)[CH2:3][C@@H:4]([C:6]([OH:8])=O)[NH2:5].[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[NH2:23]C(N)=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1.C(O)C>[CH3:1][CH:2]1[C:9](=[O:11])[NH:23][C:6](=[O:8])[CH:4]([N:5]2[C:15](=[O:16])[C:14]3[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:17])[CH2:3]1

Participants

7

Reactant 4

HCID 1176UreaHCID 6811Phthalic AnhydrideHCID 7918Acetic AnhydrideHCID 4409594-Methyl-L-glutamate

Product 1

HCID 10778555HCID 10778555, compoundYield 130.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

2.00 g (11 mmoles) 4-methylglutamic acid and 1.95 g (13 mmoles) phthalic anhydride were heated for 6 hours under reflux in 15 ml of dry pyridine. After removing the solvent by distillation, the residue was heated to boiling for 1 hour in 10 ml acetic anhydride. The solid which precipitated on cooling was filtered off under suction and the filtrate was concentrated. After treating the filtrate with ether, the precipitate which formed was filtered off under suction and the purified precipitates were recrystallised from absolute toluene. 2.00 g (7 mmoles) of the crystalline material and 0.23 g (3.8 mmoles) urea were well mixed and 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 6 ml ethanol in succession. The precipitated solid was filtered off under suction and recrystallised from DMF/water. 1.35 g (67% theoretical) 2-(5-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dihydro-2H-isoindole-1,3-dione (1) were obtained, with a melting point of 270 to 272° C.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation
  3. temperaturethe residue was heated
  4. customThe solid which precipitated
  5. temperatureon cooling
  6. filtrationwas filtered off under suction
  7. concentrationthe filtrate was concentrated
  8. additionAfter treating the filtrate with ether
  9. customthe precipitate which formed
  10. filtrationwas filtered off under suction
  11. customthe purified precipitates
  12. customwere recrystallised from absolute toluene
  13. waitwere fused on an oil bath at about 200° C. for 30 minutes
  14. temperatureThe solidified melt was heated briefly
  15. filtrationThe precipitated solid was filtered off under suction
  16. customrecrystallised from DMF/water

Sources & evidence

ORD record
ord-510e24d5507d4b7bab12f0294f75f439
Source dataset
uspto-grants-2000_08
Patent number
US06110941

Reaction notes

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