Sodium Iodide → HCID 43729495, compound

HRID 1964001Notes

Reaction equation

HRID 1964001 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].Br[CH2:11][CH:12]([CH3:14])[CH3:13].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH:7][CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 27348055-Bromo-o-toluidine

Product 1

HCID 43729495HCID 43729495, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7.44 g (40.0 mmol) of 5-bromo-2-methylaniline, 8.22 g (60.0 mmol) of 1-bromo-2-methyl propane, 8.99 g (60.0 mmol) of sodium iodide and 8.29 g (60.0 mmol) of potassium carbonate were stirred in a DMF solvent at 70° C. for 22 hours. To the reaction mixture was added water and extracted with ethyl acetate. The organic layer was separated, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography to give 5.92 g of 5-bromo-2-methyl-N-(2-methylpropyl)aniline (yield: 61%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was separated
  7. custompurified

Sources & evidence

ORD record
ord-d891f8804ffd4f9d8f77df12c97e46a5
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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