Sulfuric Acid → 3,5-diiodonitrobenzene

HRID 420400Notes

Reaction equation

HRID 420400 reaction equation
OS(O)(=O)=O.[I:6][C:7]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([I:17])[C:8]=1N.NC1C=CC=CC=1.N([O-])=O.[Na+]>CCO>[I:6][C:7]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([I:17])[CH:8]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6115AnilineHCID 793862,6-Diiodo-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 121342563,5-diiodonitrobenzeneYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an iced-cooled solution of concentrated H2SO4 (95-98%, 100 mL) was added in small portions 2,6-diiodo-4-nitroaniline (25 g, 64.1 mmol). After complete dissolution of the aniline, NaNO2 (9.7 g, 141 mmol) was added at 0° C. and stirred for 2 h at this temperature. Then, the viscous black solution was poured into ice (500 g) and any solid material was filtered off. The brown filtrate obtained was carefully poured into a refluxed solution of CuSO4.5H2O (1.0 g, 6.4 mmol) in EtOH (300 mL) and stirred at reflux for 2 h to reduce the diazonium salt. After cooling to room temperature, 3,5-diiodonitrobenzene precipitated from the reaction mixture. After filtration, the product was then recrystallized with hot EtOH to give 15.92 g (67%) of fine brown needles. HR-MS-EI(+): calculated for C6H3I2NO2 [M] 374.8253, found 374.8354.

Workup

  1. additionwas added at 0° C.
  2. filtrationany solid material was filtered off
  3. customThe brown filtrate obtained
  4. stirringstirred
  5. temperatureat reflux for 2 h
  6. custom3,5-diiodonitrobenzene precipitated from the reaction mixture
  7. filtrationAfter filtration
  8. customthe product was then recrystallized with hot EtOH

Sources & evidence

ORD record
ord-522211a9492c4efcb16e45114db4baf9
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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