Iodine → 4-Chloro-2-iodo-6-nitroaniline

HRID 1802823Notes

Reaction equation

HRID 1802823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[I:12]I>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[NH2:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[I:12]

Participants

5

Reactant 2

HCID 807IodineHCID 69794-Chloro-2-nitroaniline

Product 1

HCID 121435644-Chloro-2-iodo-6-nitroanilineYield 69.8%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

Commercially available 4-chloro-2-nitro-phenylamine (17.4 g, 131.5 mmol) was dissolved in ethanol (300 mL), and thereto silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol) were added. The mixture was stirred for 8 hours at room temperature. At the end of reaction, the mixture was filtered using celite and washed with 100 ml of ethylacetate and concentrated. To the concentrate, added water and extracted with ethylacetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate to give 2-amino-5-chloro-3-nitro-phenyliodide (27.4 g, Yield 69%).

Workup

  1. customAt the end of reaction
  2. filtrationthe mixture was filtered
  3. washwashed with 100 ml of ethylacetate
  4. concentrationconcentrated
  5. additionTo the concentrate, added water
  6. extractionextracted with ethylacetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-c3fad32b36274f93977ed88a6fa3cb3e
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

Loading…