Iodine → 4-Iodo-2,6-dimethylbenzenamine

HRID 589558Notes

Reaction equation

HRID 589558 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[I:10]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1.N1C=CC=CC=1>[I:10][C:7]1[CH:6]=[C:5]([CH3:9])[C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=1

Participants

6

Reactant 3

HCID 807IodineHCID 68962,6-DimethylanilineHCID 24477Sodium Thiosulfate

Product 1

HCID 2789424-Iodo-2,6-dimethylbenzenamineYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-dimethyl aniline (50 gm) in 1,4-dioxane (400 ml) and pyridine (40 ml) was added iodine (157.3 gm) slowly at 0° C. The solution was stirred for 1 hour at 0° C. and the temperature was raised to room temperature. The solution was stirred for 1 hour at room temperature and then added a saturated solution of sodium thiosulfate. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic layers were dried with anhydrous sodium sulfate and the solvent was evaporated in vacuum to obtain 91.8 gm of 4-iodo-2,6-dimethyl benzenamine.

Workup

  1. temperaturethe temperature was raised to room temperature
  2. stirringThe solution was stirred for 1 hour at room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. dry with materialThe combined organic layers were dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-394692fda96645f988ef30d8fef96a08
Source dataset
uspto-grants-2016_01
Patent number
US09233935B2

Reaction notes

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