Water → 3-[5-(Imidazo[1,2-a]pyridin-5-yl)pentyl]oxazolidine-2,4-dione

HRID 357014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357014
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[K].[O:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].[I-].[Na+].O>CN(C)C=O>[N:15]1[CH:14]=[CH:13][N:12]2[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:19]3[C:20](=[O:22])[CH2:21][O:17][C:18]3=[O:23])=[CH:8][CH:9]=[CH:10][C:11]=12

Komponenten

6

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 189366765-(5-Chloropentyl)imidazo[1,2-a]pyridineHCID 70204806Oxazolidine-2,4-dione potassium salt

Produkt 1

HCID 189366443-[5-(Imidazo[1,2-a]pyridin-5-yl)pentyl]oxazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 15.59 g (70 mmol) of 5-(5-chloropentyl)imidazo[1,2-a]pyridine and 9.74 g (70 mmol) of oxazolidine-2,4-dione potassium salt in 300 ml of N,N-dimethylformamide, 10.49 g (70 mmol) of sodium iodide was added, followed by stirring at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate→ethyl acetate/ethanol=10/1) to yield 11.90 g (59.2%, light orange crystal) of the desired product.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate→ethyl acetate/ethanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-466c8fb488524e4287f8b639b447d684
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

Notizen zur Reaktion

Wird geladen…