2-Bromotoluene → 1-o-tolyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione

HRID 1984618

Reaktionsgleichung

Reaktionsgleichung von HRID 1984618
[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+].Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].C(OCC)(=O)C>CN1CCCC1=O>[C:19]1([CH3:24])[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][CH:2]12

Komponenten

6

Edukt 4

HCID 72362-BromotolueneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 65955Dimiracetam

Produkt 1

HCID 117363641-o-tolyl-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dioneAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a solution of tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione (1.3 g, 9.28 mmol, prepared as described in J. Med. Chem. 36, 4214, 1994) in N-methylpyrrolidone (NMP, 12 cc), Cul (0.5 g, 2.62 mmol), K2CO3 (1.3 g, 9.28 mmol) and 2-bromotoluene (6 g, 35 mmol) were added under stirring. The suspension was heated in a microwave apparatus (250 Watt) for 1 h. 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 Ma2SO4, filtered and concentrated to dryness. The residue was triturated with Et2O. The solid was filtered, and crystallized the first time with IPrOH and then with AcOEt to yield 0.33 g of the title compound, mp=138-139° C.

Aufarbeitung

  1. temperatureThe suspension was heated in a microwave apparatus (250 Watt) for 1 h
  2. filtrationthe solid was filtered
  3. washThe organic phase was washed with water
  4. extractionthe aqueous phase was re-extracted with CH2Cl2
  5. customdried over Ma2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was triturated with Et2O
  9. filtrationThe solid was filtered
  10. customcrystallized the first time with IPrOH

Quellen und Nachweise

ORD-Eintrag
ord-7cc629a470e8418882b2768294ed62ac
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544705B2

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