Sodium Azide → 2-Azido-1,3-diiodo-5-nitrobenzene

HRID 358226Notes

Reaction equation

HRID 358226 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]=1[NH2:4].[N-:13]=[N+:14]=[N-].[Na+]>S(=O)(=O)(O)O.O>[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([I:12])[C:3]=1[N:4]=[N+:13]=[N-:14]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 793862,6-Diiodo-4-nitroaniline

Product 1

HCID 204496312-Azido-1,3-diiodo-5-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

5 g of 2,6-diiodo-4-nitroaniline was dissolved in 20 ml of conc. sulfuric acid and cooled with ice. Sodium nitrite previously vacuum-dried was added to the solution in portions to effect the diazotization reaction at 0°-5° C. The reaction product was added dropwise to ice-water to dilute the sulfuric acid. A solution of 1.4 g of sodium azide in 10 cc of water was added dropwise to the mixture, stirred for about one hour, filtered and washed with water. After the recrystallization from ethanol followed by drying, 2,6-diiodo-4-nitroazidobenzene was obtained.

Workup

  1. temperaturecooled with ice
  2. dry with materialSodium nitrite previously vacuum-dried
  3. additionwas added to the solution in portions
  4. customthe diazotization reaction at 0°-5° C
  5. filtrationfiltered
  6. washwashed with water
  7. customAfter the recrystallization from ethanol
  8. customby drying

Sources & evidence

ORD record
ord-2757f3ac0b2f43d486b9d327aa609406
Source dataset
uspto-grants-1984_08
Patent number
US04465768

Reaction notes

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