Reaktion #43389

Reaktionsgleichung

tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione

K2CO3

Iodobenzene

Ethyl acetate

→

title compound

Ausbeute 11.7%

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

Ausbeute 11.7%

Lösungsmittel

N-methylpyrrolidone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe suspension was heated in a microwave apparatus (250 Watt) for 45 min
2. 2
   Filtrationthe solid was filtered
3. 3
   WaschenThe organic phase was washed with water
4. 4
   Extraktionthe aqueous phase was re-extracted with CH2Cl2
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to dryness
8. 8
   SonstigeThe residue was triturated with isopropyl ether
9. 9
   FiltrationThe solid was filtered
10. 10
    Sonstigetriturated with water
11. 11
    Filtrationfiltered

Vorschrift

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.

Quelle