Sulfuric Acid → Benzenesulfonic acid, 3,4-diamino-

HRID 2205155Notes

Reaction equation

HRID 2205155 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[S:9](=O)(=[O:12])([OH:11])[OH:10]>>[NH2:7][C:2]1[CH:3]=[C:4]([S:9]([OH:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:1]=1[NH2:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 7243O-Phenylenediamine

Product 1

HCID 81986Benzenesulfonic acid, 3,4-diamino-

Procedure

Concentrated sulfuric acid (200 mL) was added to benzene-1,2-diamine (20 g, 184.95 mmol, 1.00 equiv) at −40° C., and the solution was stirred for 30 minutes at room temperature, then overnight at 140° C. in an oil bath. Upon cooling to room temperature, the reaction was quenched by 500 g of ice. The solids were collected by filtration, and the crude product was purified by re-crystallization from water affording 9.8 g (28%) of 3,4-diaminobenzenesulfonic acid as a white solid.

Workup

  1. customovernight
  2. customat 140° C.
  3. temperatureUpon cooling to room temperature
  4. customthe reaction was quenched by 500 g of ice
  5. filtrationThe solids were collected by filtration
  6. customthe crude product was purified by re-crystallization from water affording 9.8 g (28%) of 3,4-diaminobenzenesulfonic acid as a white solid

Sources & evidence

ORD record
ord-1cf0da9554a14975a33c8f092081955c
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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