Hydrochloric Acid → HCID 18973065, compound

HRID 2394352Notes

Reaction equation

HRID 2394352 reaction equation
[Na].[C:2]1([S:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][N:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:21][C:22]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=O)C.Cl>C(O)C>[C:2]1([S:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][N:17]=2)[NH:14][C:13](=[O:18])[CH:12]3[C:22](=[O:21])[C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 189730441,3-Dihydro-5-(phenylthio)-2H-pyrrolo[2,3-c]pyridin-2-one

Product 1

HCID 18973065HCID 18973065, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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).

Workup

  1. additionwas added
  2. temperatureThe mixture was then heated
  3. temperatureat reflux for 30 hours
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried
  6. additionFractions containing the desired product, 5-phenylthio-3-(2-thenoyl)-6-azaoxindole
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ccd700a5a4f044109045b7572a9a7264
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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