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

HRID 1081743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081743
[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.C(OCC)(=O)C>[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

7

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 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

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 extratced 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. customdried
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by column chromatography [eluent:ethyl acetate/hexane (1:1)→ethyl acetate/hexane (2:1)]

Quellen und Nachweise

ORD-Eintrag
ord-33bfcac35ff749b49b4b727683e36d3a
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587383

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