Sodium Hydroxide → HCID 23706987, compound

HRID 2418388Notes

Reaction equation

HRID 2418388 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][C:16]([Cl:19])=[CH:15][CH:14]=3)=[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][C:16]([Cl:19])=[CH:15][CH:14]=2)=[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 20446255HCID 20446255, compound

Product 1

HCID 23706987HCID 23706987, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-(4-chlorophenylsulfinyl)indoline (4.7 g) and dioxane (30 ml) was added to a solution of sodium hydroxide (2.5 g) in water (30 ml), and the mixture was refluxed with stirring for 15 hrs. Dioxane was distilled off from the reaction mixture in vacuo, and the residue was dissolved in water and washed with diethyl ether. The aqueous solution was adjusted to pH 7 with 5% sulfuric acid and extracted with ethyl acetate (200 ml×2). The extract was washed with saline, dried over magnesium sulfate and then evaporated in vacuo. The residue was dissolved in 1N-sodium hydroxide (12.2 ml) under heating and the solution was concentrated in vacuo. The residue was recrystallized from ethanol twice to give powdery sodium 2-[2-amino-3-(4-chlorophenylsulfinyl)phenyl]acetate (1.5 g). mp 242°-245° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationDioxane was distilled off from the reaction mixture in vacuo
  3. dissolutionthe residue was dissolved in water
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate (200 ml×2)
  6. washThe extract was washed with saline
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in 1N-sodium hydroxide (12.2 ml)
  10. temperatureunder heating
  11. concentrationthe solution was concentrated in vacuo
  12. customThe residue was recrystallized from ethanol twice

Sources & evidence

ORD record
ord-c3de73c403cd40259760749b014e82d8
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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