Ethyl Acetate → 1-Phenyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione

HRID 15111

Reaction equation

HRID 15111 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][CH:2]12.C([O-])([O-])=O.[K+].[K+].I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)(=O)C>CN1CCCC1=O.[Cu]I>[C:18]1([N:1]2[C:5](=[O:6])[CH2:4][N:3]3[C:7](=[O:10])[CH2:8][CH2:9][CH:2]23)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 65955Dimiracetam

Product 1

HCID 112413861-Phenyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dioneYield 11.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione (1 g, 7.14 mmol; prepared as described in J. Med. Chem. 36, 4214-4220, 1994,) in N-methylpyrrolidone (NMP, 12 cc), CuI (0.2 g, 1.05 mmol), K2CO3 (1 g, 7.14 mmol) and Iodobenzene (5 g, 24.5 mmol) were added under stirring. The suspension was heated in a microwave apparatus (250 Watt) for 45 min. Ethyl acetate was added to the suspension and the solid was filtered. The organic phase was washed with water and the aqueous phase was re-extracted with CH2Cl2. The organic phases were gathered and dried over Na2SO4, filtered and concentrated to dryness. The residue was triturated with isopropyl ether. The solid was filtered, triturated with water and filtered to yield 0.18 g of the title compound, mp=185-188° C.

Workup

  1. temperatureThe suspension was heated in a microwave apparatus (250 Watt) for 45 min
  2. filtrationthe solid was filtered
  3. washThe organic phase was washed with water
  4. extractionthe aqueous phase was re-extracted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was triturated with isopropyl ether
  9. filtrationThe solid was filtered
  10. customtriturated with water
  11. filtrationfiltered

Sources & evidence

ORD record
ord-f942b6681ad44b67b36f20f5a2643d6d
Source dataset
uspto-grants-2010_06
Patent number
US07732473B2

Linked notes

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