Sodium Hydroxide → HCID 23706960, compound

HRID 2418370Notes

Reaction equation

HRID 2418370 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([S:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[O:12])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[O:20]1CCOCC1.[OH-].[Na+:27]>O>[NH2:3][C:4]1[C:5]([S:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[O:12])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([O-:20])=[O:1].[Na+:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446146HCID 20446146, compound

Product 1

HCID 23706960HCID 23706960, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-(2-chlorophenylsulfinyl)indoline (5.0 g.), dioxane (30 ml.), sodium hydroxide (2.5 g.) and water (30 ml.) was refluxed for 8 hours with stirring. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in water under heating and filtered. The filtrate was adjusted to about pH 4 with 5% sulfuric acid and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in 1N sodium hydroxide (14.2 ml.) under heating and the solution was evaporated to dryness under reduced pressure. The oily residue was dissolved in ethanol (20 ml.) and crystallized with diethyl ether to give crystals of the captioned compound (2.9 g.). mp 248° to 251° C. (dec.).

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. temperatureunder heating
  5. filtrationfiltered
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. dissolutionThe residue was dissolved in 1N sodium hydroxide (14.2 ml.)
  11. temperatureunder heating
  12. customthe solution was evaporated to dryness under reduced pressure
  13. dissolutionThe oily residue was dissolved in ethanol (20 ml.)
  14. customcrystallized with diethyl ether
  15. customto give crystals of the captioned compound (2.9 g.)

Sources & evidence

ORD record
ord-66ee777a9b014657aa6b4a7dcddbaf8e
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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