Acetone → HCID 22506858, compound

HRID 985570Notes

Reaction equation

HRID 985570 reaction equation
[CH3:1][C:2]1[CH:7]=CC(C)=C[C:3]=1[NH:9][C:10](=O)C(F)(F)F.[I-].[K+].Cl[CH2:19][C:20]([CH3:22])=[CH2:21].[OH-].[K+].[CH3:25][C:26]([CH3:28])=O>O>[CH3:25][C:26]1[CH:28]=[CH:21][C:20]([CH3:22])=[CH:19][C:10]=1[NH:9][CH2:3][C:2]([CH3:7])=[CH2:1]

Participants

7

Reactant 5

HCID 180AcetoneHCID 4875Potassium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 14797Potassium HydroxideHCID 139794Acetamide, N-(2,5-dimethylphenyl)-2,2,2-trifluoro-

Product 1

HCID 22506858HCID 22506858, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-(2,5-dimethylphenyl)-2,2,2-trifluoroacetoamide (5.87 g, 27.0 mmol) in acetone (50 ml) were added potassium iodide (4.49 g 27.0 mmol), 3-chloro-2-methyl-1-propene (8.0 ml, 81 mmol) and pulverized 85% potassium hydroxide (5.3 g, 80 mmol), and the mixture was heated under reflux for 1 hour. Water was added to the reaction mixture and the mixture was extracted twice with hexane. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=100:1, followed by 50:1) to obtain 4.11 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionthe mixture was extracted twice with hexane
  4. washwashed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=100:1, followed by 50:1)

Sources & evidence

ORD record
ord-7303f7fc175a4bd2ae1ff982b2c7d2b2
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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