Hydrochloric Acid → HCID 18973065, compound

Participants

Reaction Steps

Pellets of sodium metal (264 mg, 11.5 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, a slurry of 5-phenylthio-6-azaoxindole (560 mg, 2.3 mmol) in ethanol (5 mL) was added. The mixture was warmed to 50° C. at which point ethyl-2-thiophene carboxylate (0.55 mL, 4.6 mmol) was added. The mixture was then heated at reflux for 30 hours. After cooling to room temperature, the mixture was poured into ice/water and the pH adjusted to 1 by addition of 6N HCl solution. The precipitated solid was collected by filtration, dried and subjected to flash chromatography on silica gel using 9:1 chloroform/methanol as eluant. Fractions containing the desired product, 5-phenylthio-3-(2-thenoyl)-6-azaoxindole were combined and evaporated under reduced pressure to leave a gold solid (620 mg, 76%); m.p. 248°-252° C. (dec).

Provenance & Evidence