Dimethylformamide → 1-[3-(tert-Butyl)-5-(dimethylamino)-4-methoxyphenyl]-1-ethanone

HRID 1295947Notes

Reaction equation

HRID 1295947 reaction equation
C(=O)([O-])[O-].[K+].[K+].CI.NC1[CH:11]=[C:12]([C:22](=[O:24])[CH3:23])[CH:13]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:15]=1[O:16][CH3:17].C(OCC)(=O)C.[CH3:31][N:32]([CH3:35])[CH:33]=O>>[C:18]([C:14]1[CH:13]=[C:12]([C:22](=[O:24])[CH3:23])[CH:11]=[C:33]([N:32]([CH3:35])[CH3:31])[C:15]=1[O:16][CH3:17])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22929815HCID 22929815, compound

Product 1

HCID 589100481-[3-(tert-Butyl)-5-(dimethylamino)-4-methoxyphenyl]-1-ethanone

Procedure

Potassium carbonate (8.5 g, 62 mmol) and methyl iodide (8.8 g, 62 mmol) were added to a solution of 1-[3-amino-5-(tert-butyl)-4-methoxyphenyl]-1-ethanone (6 g, 21 mmol) in dimethylformamide (50 ml) and the mixture was stirred at room temperature for 13 hours. Ethyl acetate was added, the reaction mixture was washed with water and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.9 g) as a light yellow oil.

Workup

  1. washthe reaction mixture was washed with water and brine in that order
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-313c1fc3c38c4b4499fc381aff5aafcc
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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