Iodine → 4-Iodo-2,6-dimethylbenzenamine

HRID 2274021Notes

Reaction equation

HRID 2274021 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.CN1CCCC1=O>[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 89.3%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 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 N-methylpyrrolidone (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 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-5407fc16acc14e34a5f9995983dc505a
Source dataset
uspto-grants-2015_09
Patent number
US09126949B2

Reaction notes

Loading…