Acetic Acid → 2,5-dibromo-4-nitro-N-benzenesulphonylaniline

HRID 4232Notes

Reaction equation

HRID 4232 reaction equation
C(O)(=O)C.[N:5]([O-:7])=[O:6].[Na+].[Br:9][C:10]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:11]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].[N+]([O-])(O)=O>O>[Br:9][C:10]1[CH:25]=[C:24]([N+:5]([O-:7])=[O:6])[C:23]([Br:26])=[CH:22][C:11]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 20152003HCID 20152003, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 201520062,5-dibromo-4-nitro-N-benzenesulphonylaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 250 ml of acetic acid, diluted with 130 ml of water, are added: 1.5 g of sodium nitrite, 0.13 mole of 2,5-dibromo-N-benzenesulphonylaniline prepared in the previous stage and 0.78 mole (32.5 ml) of nitric acid (d=1.52). The reaction mixture is heated for 1 hour at 90° C. The reaction mixture, cooled beforehand, is poured onto 1 kg of ice and the expected product precipitates. It is filtered off, washed to neutrality and then recrystallized from acetic acid; it melts at 148° C.

Workup

  1. additionare added
  2. temperatureThe reaction mixture, cooled beforehand
  3. customthe expected product precipitates
  4. filtrationIt is filtered off
  5. washwashed to neutrality
  6. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-617bfdd769eb46abb48d202834543d87
Source dataset
uspto-grants-1988_02
Patent number
US04725283

Reaction notes

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