Potassium Iodide → HCID 14914462, compound

HRID 1700423Notes

Reaction equation

HRID 1700423 reaction equation
N([O-])=O.[Na+].[C:5]([C:9]1[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([CH:15]=1)N)([CH3:8])([CH3:7])[CH3:6].[I-:18].[K+]>O>[C:5]([C:9]1[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([I:18])[CH:15]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 41763185-tert-Butyl-o-anisidineHCID 23668193Sodium Nitrite

Product 1

HCID 14914462HCID 14914462, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
5 °C

Procedure

A solution of 8 g (0.11 mol) of sodium nitrite in 25 ml of water was added dropwise to a solution of 20 g (0.11 mol) of 5-tert-butyl-2-methoxyaniline in 120 ml of water/conc. HCL (1:1) cooled to 5° C. After stirring at 5° C. for 15 min, a solution of 19.1 g (0.11 mol) of potassium iodide in 25 ml of water was added dropwise and the solution obtained was stirred at RT for 4 h. It was extracted several times with DCM, and the separated organic phase was washed with 10% strength NaHSO3 solution and water, dried over Na2SO4, and concentrated. Chromatographic purification of the residue which remained on SiO2 using EA/heptane (1:40) yielded 27 g of the title compound in the form of a pale red oil.

Workup

  1. customthe solution obtained
  2. stirringwas stirred at RT for 4 h
  3. extractionIt was extracted several times with DCM
  4. washthe separated organic phase was washed with 10% strength NaHSO3 solution and water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customChromatographic purification of the residue which

Sources & evidence

ORD record
ord-2a07955072d34449ae5ce5f2bad4dc78
Source dataset
uspto-grants-2002_02
Patent number
US06350778B1

Reaction notes

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