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

HRID 235546ノート

反応式

HRID 235546 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9399bf28d40d47789b803f26d0f19d76
出典データセット
uspto-grants-1987_02
特許番号
US04640703

反応ノート

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