Sulfuric Acid → 3,5-diiodonitrobenzene

HRID 1741580Notes

Reaction equation

HRID 1741580 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.[I:10][C:11]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([I:21])[C:12]=1N>C(O)(=O)C.C(O)C>[I:10][C:11]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([I:21])[CH:12]=1

Participants

6

Reactant 3

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

Product 1

HCID 121342563,5-diiodonitrobenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

13.8 G (0.2M) of solid sodium nitrite were slowly added to stirred concentrated sulfuric acid at 0° C. The resulting thick mixture was stirred at 0° C. for 10 mins. A suspension of 68.28 G (0.175M) of finely powdered 2,6-diiodo-4-nitroaniline in 175 mL of glacial acetic acid was added portionwise cautiously to the above mixture at 0° C. over a period of 25 minutes. This mixture was then stirred 30 mins, and then added to a vigorously stirred suspension of 4 G of cuprous oxide in 420 mL of absolute ethanol over a period of 25 minutes. Vigorous effervescence was observed during this addition. The resulting mixture was stirred 20 mins. at room temperature and then heated to reflux for 30 mins. After cooling, this reaction mixture was poured into large amount of ice. Solid separated was filtered, and washed with water. This solid was dissolved in minimum amount of chloroform, and dried over anhydrous magnesium sulfate. Solvent removal gave 62 G of 3,5-diiodo-nitrobenzene as light yellow solid.

Workup

  1. additionwas added portionwise cautiously to the above mixture at 0° C. over a period of 25 minutes
  2. stirringThis mixture was then stirred 30 mins
  3. additionVigorous effervescence was observed during this addition
  4. stirringThe resulting mixture was stirred 20 mins
  5. temperatureat room temperature and then heated
  6. temperatureto reflux for 30 mins
  7. temperatureAfter cooling
  8. additionthis reaction mixture was poured into large amount of ice
  9. customSolid separated
  10. filtrationwas filtered
  11. washwashed with water
  12. dissolutionThis solid was dissolved in minimum amount of chloroform
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customSolvent removal

Sources & evidence

ORD record
ord-a6a9258aa61f447894dd56e894eb8f74
Source dataset
uspto-grants-1994_08
Patent number
US05334590

Reaction notes

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