Triethylamine → 5-[3-[2-(Phenyl)ethylcarbonyloxy]propylthio]imidazo[1,2-a]pyridine

HRID 5463

Reaktionsgleichung

Reaktionsgleichung von HRID 5463
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:22]1([CH2:28][CH2:29][C:30](Cl)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1([CH2:28][CH2:29][C:30]([O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

Produkt 1

HCID 233629325-[3-[2-(Phenyl)ethylcarbonyloxy]propylthio]imidazo[1,2-a]pyridineAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added 3-phenylpropionyl chloride (1.01 g, 5.99 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 2 hours. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent: hexane/acetone (1:1)] to obtain 1.37 g of the desired product (84.2%, yellow oily product).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 2 hours
  2. washThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography [eluent: hexane/acetone (1:1)]

Quellen und Nachweise

ORD-Eintrag
ord-2079fc0d693f44d2b7680a1a439cd964
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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