Potassium Carbonate → HCID 22313738, compound

HRID 965909Notes

Reaction equation

HRID 965909 reaction equation
Br[CH2:2][C:3]#[C:4][CH3:5].[C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])(=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.[I-].[Na+]>[CH2:2]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:6](=[O:8])[CH3:7])[C:3]#[C:4][CH3:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 119722-AcetamidophenolHCID 27568621-Bromo-2-butyne

Product 1

HCID 22313738HCID 22313738, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-bromo-2-butine (1.39 g (10.4 mmol), 2-acetamidophenol (1.58 mg, 10.4 mmol), anhydrous potassium carbonate (1.44 g, 10.4 mmol) and sodium iodide (30 mg) in butanone (50 ml) was heated over night to reflux. After that the reaction mixture was filtrated, the filtrate was evaporated and the resulting residue was taken up by ethyl acetate. The obtained solution was washed with 5-proz. sodium hydroxide, brine and water, dried over sodium sulfate and evaporated. The crude was recrystallized out of heptane/MTB (1:1) yielding in 1.57 g (74%) of a light brown needles.

Workup

  1. temperaturewas heated over night
  2. temperatureto reflux
  3. filtrationAfter that the reaction mixture was filtrated
  4. customthe filtrate was evaporated
  5. washThe obtained solution was washed with 5-proz
  6. dry with materialsodium hydroxide, brine and water, dried over sodium sulfate
  7. customevaporated
  8. customThe crude was recrystallized out of heptane/MTB (1:1)

Sources & evidence

ORD record
ord-97e8f8213494487fb096384322eb8472
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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