Dibutylamine → 4-Dibutylamino-3,5-dimethoxybenzene

HRID 85303Notes

Reaction equation

HRID 85303 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:12]([NH:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>O1CCOCC1>[CH2:12]([N:16]([CH2:17][CH2:18][CH2:19][CH3:20])[C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[O:9][CH3:10])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8148DibutylamineHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 680088654-Dibutylamino-3,5-dimethoxybenzeneYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a stream of argon, to 300 ml of dioxane were added 21.7 g (100 mmol) of 3,5-dimethoxybromobenzene and 13.0 g (100 mmol) of dibutylamine, and 22.0 g (110 mmol) of potassium bistrimethylsilylamide was added thereto with stirring. After well-stirred, the mixture was heated under reflux with stirring overnight. The reactant was poured into 2 L of ice water and subjected to 3 times of extraction with 200 ml of chloroform. Washing with a saturated saline solution, drying over anhydrous magnesium sulfate, and concentration were performed. The residue was purified by silica gel chromatography to give 23.4 g (yield: 88%) of 4-dibutylamino-3,5-dimethoxybenzene as a colorless transparent oily matter.

Workup

  1. additionwas added
  2. stirringAfter well-stirred
  3. temperaturethe mixture was heated
  4. temperatureunder reflux
  5. stirringwith stirring overnight
  6. extractionsubjected to 3 times of extraction with 200 ml of chloroform
  7. washWashing with a saturated saline solution
  8. dry with materialdrying over anhydrous magnesium sulfate, and concentration
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-42590c32c5cc497694e076a62762d371
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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