Sulfuric Acid → 3,5-diiodonitrobenzene

HRID 1743014Notes

Reaction equation

HRID 1743014 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.[N+:10]([C:13]1[CH:19]=[C:18]([I:20])[C:16](N)=[C:15]([I:21])[CH:14]=1)([O-:12])=[O:11]>C(O)(=O)C.C(O)C>[I:20][C:18]1[CH:19]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[C:15]([I:21])[CH:16]=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 (0.2 M) of sodium nitrite was added portionwise slowly to 96 mL of conc. sulfuric acid at 0° C. The resulting thick mixture was stirred at 0° C. for 10 minutes. A suspension of 68.25 g (0.175 M) of finely powdered 4-nitro-2,6-diiodoaniline in 175 mL of glacial acetic acid was added cautiously portionwise to the above mixture at 0° C. After the addition, the mixture was stirred 30 mins. The resulting slurry was then added slowly to a vigorously stirred suspension of 4 g of cuprous oxide in 420 mL of absolute ethanol over a period of 25 mins. Vigorous effervescence was observed during this addition. The resulting mixture was stirred 20 mins. at room temperature and then heated to reflux for 30 minutes. After cooling, this reaction mixture was poured onto a large amount of ice. The solid which separated was filtered, and washed with water. This solid was dissolved in a minimum amount of chloroform, dried over anhyd. magnesium sulfate, and the solvent was removed to give 62 g of 3,5-diiodnitrobenzene as a yellow solid. ##STR135##

Workup

  1. additionwas added cautiously portionwise to the above mixture at 0° C
  2. additionAfter the addition
  3. stirringthe mixture was stirred 30 mins
  4. additionVigorous effervescence was observed during this addition
  5. stirringThe resulting mixture was stirred 20 mins
  6. temperatureat room temperature and then heated
  7. temperatureto reflux for 30 minutes
  8. temperatureAfter cooling
  9. additionthis reaction mixture was poured onto a large amount of ice
  10. customThe solid which separated
  11. filtrationwas filtered
  12. washwashed with water
  13. dissolutionThis solid was dissolved in a minimum amount of chloroform
  14. customdried over anhyd
  15. custommagnesium sulfate, and the solvent was removed

Sources & evidence

ORD record
ord-9ebf3091dca5485bbe86b2d315d7e6b3
Source dataset
uspto-grants-1994_08
Patent number
US05342933

Reaction notes

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