Water → 5-[2-(N-benzylmethylsulfonylamino)ethyloxy]imidazo[1,2-a]pyridine

HRID 5470

Reaktionsgleichung

Reaktionsgleichung von HRID 5470
[H-].[Na+].[CH2:3]([CH2:10][S:11]([NH:14][CH2:15][CH2:16][OH:17])(=[O:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:19]1[N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:3]([CH2:10][S:11]([NH:14][CH2:15][CH2:16][O:17][C:19]1[N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[CH:22]=[CH:21][CH:20]=1)(=[O:13])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 109537225-Chloroimidazo[1,2-A]pyridineHCID 149473952-(N-benzylmethylsulfonylamino)-1-ethanol

Produkt 1

HCID 233629515-[2-(N-benzylmethylsulfonylamino)ethyloxy]imidazo[1,2-a]pyridineAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 60% sodium hydride in oil (0.20 g, 5 mmoles) in dimethylformamide (20 ml) was added 2-(N-benzylmethylsulfonylamino)-1-ethanol (1.14 g, 5 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture was added 5-chloroimidazo[1,2-a]pyridine (0.763 g, 5 mmoles) with stirring under ice-cooling, followed by stirring at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, which was extracted with ethyl acetate and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethyl acetate/hexane (1:1)→ethyl acetate/hexane (2:1)] to obtain 0.68 g of the desired product (39.4%, pale yellow oily product).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. stirringby stirring at 80° C. for 16 hours
  6. temperatureAfter cooling
  7. extractionwas extracted with ethyl acetate
  8. customdried
  9. distillationAfter the solvent was distilled off
  10. customthe residue was purified by column chromatography [eluent: ethyl acetate/hexane (1:1)→ethyl acetate/hexane (2:1)]

Quellen und Nachweise

ORD-Eintrag
ord-e3132aba721d4308b7846406e0b07587
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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