Benzenepropanal → 5-(3-Phenylpropylidene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

HRID 357093

Reaktionsgleichung

Reaktionsgleichung von HRID 357093
[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][O:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.N1CCCC1.[C:27]1([CH2:33][CH2:34][CH:35]=O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C>[C:27]1([CH2:33][CH2:34][CH:35]=[C:18]2[O:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:9]3[N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=3)[C:19]2=[O:20])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 7707Benzenepropanal2×HCID 31268Pyrrolidine2×HCID 189367363-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

Produkt 1

HCID 572607645-(3-Phenylpropylidene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1.53 g (5 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione and 20 ml of ethanol were placed in a reaction flask, followed by stirring at 60° C. for 20 minutes, to dissolve the starting materials. After this mixture was kept standing to 50° C., an ethanol solution of 0.05 ml (0.5 mmol) of pyrrolidine was added. Next, an ethanol solution of 0.66 ml (5 mmol) of 3-phenylpropionaldehyde was added, followed by refluxing for 19 hours. Six hours later, 0.66 ml (5 mmol) of 3-phenylpropionaldehyde and 0.05 ml (0.5 mmol) of pyrrolidine were added. After the reaction mixture was cooled, the solvent was distilled off, followed by extraction with dichloromethane and water. After the organic layer was dried with sodium sulfate, the solvent was distilled off. The residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/1) to yield 26 mg (1.2%, yellow oily substance) of the desired product.

Aufarbeitung

  1. dissolutionto dissolve the starting materials
  2. customwas kept standing to 50° C.
  3. temperatureby refluxing for 19 hours
  4. temperatureAfter the reaction mixture was cooled
  5. distillationthe solvent was distilled off
  6. extractionfollowed by extraction with dichloromethane and water
  7. dry with materialAfter the organic layer was dried with sodium sulfate
  8. distillationthe solvent was distilled off
  9. washThe residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-dcae2e9c56c2411b9f4c9ab2d1acd2d0
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

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