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

HRID 4236

Reaction equation

HRID 4236 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]([F:26])=[CH:19][C:8]=1[NH:9]S(C1C=CC=CC=1)(=O)=O>O>[F:6][C:7]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]([F:26])=[CH:19][C:8]=1[NH2:9]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 201519862,5-difluoro-4-nitro-N-benzenesulphonylaniline

Product 1

HCID 2359302,5-Difluoro-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

10 ml of water are added with due care to 75 ml of concentrated sulphuric acid; the temperature rises to 70° C. 0.105 mole (33 g) of 2,5-difluoro-4-nitro-N-benzenesulphonylaniline prepared in the previous stage is then added. The temperature is maintained at 70° C. for 2 hours. The reaction mixture is poured onto 1 kg of ice and water and the expected product precipitates. After filtration and washing to neutrality the product is recrystallized from 100 ml of 96° ethanol. It melts at 153° C.

Workup

  1. customrises to 70° C
  2. additionis then added
  3. customthe expected product precipitates
  4. filtrationAfter filtration
  5. washwashing to neutrality the product
  6. customis recrystallized from 100 ml of 96° ethanol

Sources & evidence

ORD record
ord-8734794de3904b748c5147f7f30b1fb2
Source dataset
uspto-grants-1988_02
Patent number
US04725283

Linked notes

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