Hydrochloric Acid → 1-Azido-4-iodobenzene

HRID 358225Notes

Reaction equation

HRID 358225 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[N-:14]=[N+:15]=[N-].[Na+]>O>[N:6]([C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)=[N+:14]=[N-:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108934-IodoanilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 30168361-Azido-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

6 g of p-iodoaniline was dispersed in a solution comprising 25 cc of water and 7.5 cc of 36% hydrochloric acid and cooled with ice. 2.1 g of sodium nitrite was dissolved in 13 ml of water and the resulting solution was added dropwise slowly to the dispersion to effect the diazotization reaction. A solution of 2.5 g of sodium azide in 18 ml of water was added dropwise thereto and, after stirring for one hour, the mixture was subjected to extraction with benzene. After the dehydration with sodium sulfate, benzene was evaporated to obtain p-azidoiodobenzene.

Workup

  1. temperaturecooled with ice
  2. additionthe resulting solution was added dropwise slowly to the dispersion
  3. customthe diazotization reaction
  4. extractionthe mixture was subjected to extraction with benzene
  5. customAfter the dehydration with sodium sulfate, benzene was evaporated

Sources & evidence

ORD record
ord-cba0623f2a0040fda27872ab8ad69c87
Source dataset
uspto-grants-1984_08
Patent number
US04465768

Reaction notes

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