Sulfuric Acid → 4-Amino-2-chlorobenzenesulfonic acid

HRID 330869Notes

Reaction equation

HRID 330869 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[S:9](=O)(=[O:12])([OH:11])[OH:10]>>[NH2:5][C:4]1[CH:6]=[CH:7][C:8]([S:9]([OH:12])(=[O:11])=[O:10])=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 79323-Chloroaniline

Product 1

HCID 158503594-Amino-2-chlorobenzenesulfonic acid

Procedure

3-Chloroaniline, 0.4 ml, was slowly added to 4 ml of fuming sulfuric acid and stirred at room temperature overnight. While cooling to 0°, the reaction solution was poured onto water and the solid precipitated was separated by filtration. The solid filtered off was dissolved in 2N sodium hydroxide aqueous solution and conc. hydrochloric acid was then added to the solution to make the liquid acidic. The solid precipitated was taken by filtration to give the crude product of 4-amino-2-chlorobenzenesulfonic acid.

Workup

  1. temperatureWhile cooling to 0°
  2. additionthe reaction solution was poured onto water
  3. customthe solid precipitated
  4. customwas separated by filtration
  5. filtrationThe solid filtered off
  6. dissolutionwas dissolved in 2N sodium hydroxide aqueous solution
  7. additionconc. hydrochloric acid was then added to the solution
  8. customThe solid precipitated
  9. filtrationwas taken by filtration

Sources & evidence

ORD record
ord-b7f63ee575604756bdb13a8911c21361
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Reaction notes

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