Sulfuric Acid → 3,5-diiodonitrobenzene

HRID 1941927Notes

Reaction equation

HRID 1941927 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([I:12])[C:3]=1N.OS(O)(=O)=O.N([O-])=O.[Na+]>C(O)C>[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([I:12])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 793862,6-Diiodo-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 121342563,5-diiodonitrobenzeneYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To an ice-cold solution of 2,6-diiodo-4-nitro-aniline (25.0 g, 0.06 mol) in ethanol (625 mL) was added dropwise conc. H2SO4 (50.0 ml, 0.90 mol) over 30-45 min with constant stirring. The reaction mixture was heated to 60° C. and sodium nitrite (9.70 g, 0.14 mol) was added to the reaction mixture portion wise. The resulting yellow colored reaction mixture was heated slowly to 90° C. and refluxed for 2 to 2.5 h. After cooling to room temperature, the mixture was poured into ice water. The reddish brown solid thus obtained was filtered, washed with water and dried to give the desired compound as a yellow solid (17.0 g, 72%).

Workup

  1. temperatureThe resulting yellow colored reaction mixture was heated slowly to 90° C.
  2. temperaturerefluxed for 2 to 2.5 h
  3. temperatureAfter cooling to room temperature
  4. customThe reddish brown solid thus obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d0c12ca36f824ba7a9c7087759b2b5a7
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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