Reacción #444231

Ecuación de reacción

3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

acetaldehyde

piperidine

→

desired product

5-ethylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby refluxing for 5 hours
2. 2
   TemperaturaAfter the reaction mixture was cooled
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   workup.DISSOLUTIONThe residue was dissolved in chloroform
5. 5
   Lavadowashed with saturated aqueous sodium hydrogen carbonate
6. 6
   Otrodried
7. 7
   workup.DISTILLATIONafter which the solvent was distilled off
8. 8
   OtroThe residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/1→1/2)

Procedimiento

To a solution of 2.25 g (7.0 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 0.35 g (7.0 mmol) of acetaldehyde in 30 ml of ethanol, 0.07 ml (0.7 mmol) of piperidine was added, followed by refluxing for 5 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/1→1/2) to yield 0.48 g (19.7%, yellow oily substance) of the desired product.

Fuente