Hydrochloric Acid → HCID 18973020, compound

HRID 2394349Notes

Reaction equation

HRID 2394349 reaction equation
[Na].[CH:2]([O:5][C:6]1[N:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9]2)([CH3:4])[CH3:3].C([O:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=O)C.Cl>C(O)C>[CH:2]([O:5][C:6]1[N:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH:9]2[C:19](=[O:18])[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 18973058HCID 18973058, compound

Product 1

HCID 18973020HCID 18973020, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pellets of sodium metal (250 mg, 11 mmole) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-isopropoxy-4-azaoxindole (419 mg, 2.22 mmol) was added followed by ethyl-2-thiophene carboxylate (0.59 mL, 688 mg). The mixture was heated at reflux overnight and then cooled to room temperature. After pouring into ice/water, the mixture was acidified using 1N HCl solution and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was subjected to flash chromatography on silica gel eluting successively with chloroform and 49:1 chlorform/methanol. All fractions containing the desired product were combined and concentrated. The residue was again subjected to flash chromatography on silica gel eluting with chloroform. Fractions containing only the desired product were combined and concentrated to give 5-isopropoxy-3-(2-thenoyl)-4-azaoxindole as a yellow gum (300 mg, 45%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. additionAll fractions containing the desired product
  8. concentrationconcentrated
  9. additionFractions containing only the desired product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9116ef4a9a6e4f7a9ed6259e2044cba5
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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