Butanal → 3-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]-5-butylidenehydantoin

HRID 357063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357063
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][NH:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:22](=O)[CH2:23][CH2:24][CH3:25].N1CCCC1>C(O)C>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[C:18](=[CH:22][CH2:23][CH2:24][CH3:25])[NH:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12

Komponenten

5

Edukt 3

HCID 261ButanalHCID 31268PyrrolidineHCID 189366653-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]hydantoin

Produkt 1

HCID 572685863-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]-5-butylidenehydantoin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g (3.29 mmol) of 3-[4-(imidazo-[1,2-a]pyridin-5-ylthio)butyl]hydantoin and 0.30 ml (3.29 mmol) of n-butyraldehyde in 10 ml of ethanol, 0.05 ml (0.6 mmol) of pyrrolidine was added, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate/ethanol=10/1→chloroform/methanol=10/1) to yield 0.43 g (36.5%, orange-yellow oily substance) of the desired product.

Aufarbeitung

  1. temperatureby refluxing for 16 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, ethyl acetate/ethanol=10/1→chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-9195961baea547c89eb13b7921a96064
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

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