3-Aminophenol → 3-(3-Hydroxyanilino)propane-1-sulfonic acid

HRID 2050132Notes

Reaction equation

HRID 2050132 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]1[S:13](=[O:15])(=[O:14])[O:12][CH2:11][CH2:10]1>C(O)C>[S:13]([CH2:9][CH2:10][CH2:11][NH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)([OH:15])(=[O:14])=[O:12]

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 14264Propane sultone

Product 1

HCID 146199203-(3-Hydroxyanilino)propane-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 3 liters of ethanol were dissolved 330 g of m-amino-phenol and the resulting solution was boiled under reflux and to this solution were added 360 g of propanesultone all together. Continuation of the reflux yielded gradually white powdery crystal. After refluxing for 5 hours, the reaction solution was cooled with ice and the yielded white powdery crystal was collected by filtration and washed several times with ethanol. The yield was 146 g and the melting point was above 250° C.

Workup

  1. temperatureunder reflux and to this solution
  2. customContinuation of the reflux yielded gradually white powdery crystal
  3. temperatureAfter refluxing for 5 hours
  4. temperaturethe reaction solution was cooled with ice
  5. filtrationthe yielded white powdery crystal was collected by filtration
  6. washwashed several times with ethanol

Sources & evidence

ORD record
ord-da78ed19e9f64e088dfa200300f91d85
Source dataset
uspto-grants-1980_04
Patent number
US04200466

Reaction notes

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