Sodium Hydroxide → HCID 20446276, compound

HRID 2418371Notes

Reaction equation

HRID 2418371 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[O:20]1CCOCC1.[OH-].[Na+]>O>[NH2:3][C:4]1[C:5]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([OH:20])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446262HCID 20446262, compound

Product 1

HCID 20446276HCID 20446276, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-phenylsulfonylindoline (6.50 g.), dioxane (100 ml.), sodium hydroxide (3.0 g.) water (50 ml.) was refluxed under heating for 16 hours with stirring. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in water, washed with diethyl ether, adjusted to pH 4 with 1N sulfuric acid and then extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate, treated with activated charcoal and evaporated under reduced pressure. The residue was washed with a mixture of ethanol and diethyl ether and cooled. The precipitates were collected by filtration to give white crystals of 2-(2-amino-3-phenylsulfonylphenyl)acetic acid (3.60 g.). mp 218° to 220° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 16 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washwashed with diethyl ether
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. additiontreated with activated charcoal
  10. customevaporated under reduced pressure
  11. washThe residue was washed with a mixture of ethanol and diethyl ether
  12. temperaturecooled
  13. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-9287135cd02d4303a441c4df919e181b
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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