Methyl iodide → 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyano-N-methylamide

HRID 845690Notes

Reaction equation

HRID 845690 reaction equation
[C:1]([NH:3][C:4](=[O:25])[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[CH3:6])#[N:2].[C:26](=O)([O-])[O-].[K+].[K+].CI>CC(CC)=O>[C:1]([N:3]([CH3:26])[C:4](=[O:25])[CH:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[CH3:6])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 855231952-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyanamide

Product 1

HCID 540085292-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyano-N-methylamideYield 59.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

17.5 g (0.05 mole) of 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyanamide are dissolved in 60 ml of methylethyl ketone and with 7.6 g (0.055 mole) of potassium carbonate heated for 30 minutes to reflux. Then 3.6 ml (0.057 mole) of methyl iodide are added at 30° C. to the colourless suspension and the mixture is stirred for two hours at the same temperature. The reaction mixture is then filtered and the filtrate is concentrated by evaporation. The oily residue is chromatographed through silica gel eluted with petroleum ether/ethyl acetate (3:1) and the main fraction is concentrated by evaporation, affording 10.9 g (59.9% of theory) of 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyano-N-methylamide as a clear, colourless oil with a refractive index of nD23 =1.5228.

Workup

  1. temperatureheated for 30 minutes
  2. temperatureto reflux
  3. filtrationThe reaction mixture is then filtered
  4. concentrationthe filtrate is concentrated by evaporation
  5. customThe oily residue is chromatographed through silica gel
  6. washeluted with petroleum ether/ethyl acetate (3:1)
  7. concentrationthe main fraction is concentrated by evaporation

Sources & evidence

ORD record
ord-a303ab9e071e48c3ac9c4a504f8e9d64
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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