Sulfuric Acid → 2,5-dibromo-4-nitroaniline

HRID 4233Notes

Reaction equation

HRID 4233 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]([Br:26])=[CH:19][C:8]=1[NH:9]S(C1C=CC=CC=1)(=O)=O>O>[Br:6][C:7]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]([Br:26])=[CH:19][C:8]=1[NH2:9]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 201520062,5-dibromo-4-nitro-N-benzenesulphonylaniline

Product 1

HCID 111506072,5-dibromo-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

15 ml of water are added, with due care, to 115 ml of concentrated sulphuric acid; the temperature rises to 70° C. 0.105 mole (46 g) of 2,5-dibromo-4-nitro-N-benzenesulphonylaniline are then added. The temperature is maintained at 70°-78° C. for 2 hours. The reaction mixture is poured into 1 kg of ice and water; the expected product precipitates. After filtration and washing to neutrality the product is recrystallized from 450 ml of ethanol. It melts at 178° C.

Workup

  1. customrises to 70° C
  2. temperatureThe temperature is maintained at 70°-78° C. for 2 hours
  3. customthe expected product precipitates
  4. filtrationAfter filtration
  5. washwashing to neutrality the product
  6. customis recrystallized from 450 ml of ethanol

Sources & evidence

ORD record
ord-dbe92f0c312a4853a6a2bebab89efc08
Source dataset
uspto-grants-1988_02
Patent number
US04725283

Reaction notes

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