Ethyl 2-thenoate → HCID 18973016, compound

HRID 2394338Notes

Reaction equation

HRID 2394338 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](OCC)=[O:18]>C(O)C>[C:13]1([C:17]([CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[N:7][CH:6]=3)[NH:2][C:3]2=[O:11])=[O:18])[S:12][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 156920311,3-Dihydro-2H-pyrrolo[3,2-c]pyridin-2-one

Product 1

HCID 18973016HCID 18973016, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pellets of sodium metal (1.15 g, 50 mmol) were added to dry ethanol (30 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-azaoxindole (1.40 mg, 10.4 mmol) was added followed by ethyl 2-thiophenecarboxylate (2.7 mL, 20.1 mmol). The mixture was heated under nitrogen at reflux for 1 hour. At this point, the volume of the mixture was reduced 50% by distillation of ethanol at atmospheric pressure. The mixture was cooled and poured into ice/water. The resulting solution was filtered to remove a small amount of insoluble material which was washed well with water. Upon acidification of the filtrate to pH 7 with 6N HCl solution, the product precipitated. This was collected by filtration, washed with water and dried in the air to yield the title compound as a yellow/brown solid (2.0 g, 83%).

Workup

  1. temperatureThe mixture was heated under nitrogen
  2. temperatureat reflux for 1 hour
  3. distillationby distillation of ethanol at atmospheric pressure
  4. temperatureThe mixture was cooled
  5. additionpoured into ice/water
  6. filtrationThe resulting solution was filtered
  7. customto remove a small amount of insoluble material which
  8. washwas washed well with water
  9. customUpon acidification of the filtrate to pH 7 with 6N HCl solution, the product precipitated
  10. filtrationThis was collected by filtration
  11. washwashed with water
  12. customdried in the air

Sources & evidence

ORD record
ord-4838233a9663469a9c2bc0168cf40455
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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