Diethyl Ether → HCID 22929663, compound

HRID 1295954Notes

Reaction equation

HRID 1295954 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:25][CH2:26][O:27][CH2:28][CH3:29]>CN(C)C=O.BrOBr>[C:10]([C:6]1[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[CH:3]=[C:2]([N:1]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:7]=1[O:8][CH3:9])([CH3:11])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 22929815HCID 22929815, compound

Product 1

HCID 22929663HCID 22929663, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14513628Dibromine monoxideSolvent

Conditions

Temperature
80 °C

Procedure

After dissolving 1-[3-amino-5-(tert-butyl)-4-methoxyphenyl]-1-ethanone (180 g) in dimethylformamide (800 ml), dibromoether (125 ml), potassium carbonate (225 g) and sodium iodide (12.2 g) were added and the mixture was stirred at 80° C. for 48 hours. The reaction mixture was cooled to room temperature, 3 l of ether was added and the mixture was washed 3 times with water. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (76 g) as yellow crystals.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washthe mixture was washed 3 times with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b0da6e4a1ba24b8c9cd8bd4cc4bb124f
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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