Methyl iodide → alpha-(p-Tolylthio)-alpha-(m-phenoxyphenyl)propionitrile

HRID 1759421ノート

反応式

HRID 1759421 の反応式
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[C:9]#[N:10])=[CH:3][CH:2]=1.[CH3:25][O-].[Na+].CI.[Cl-].[NH4+]>CO>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)([CH3:25])[C:9]#[N:10])=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 12945139alpha-(p-Tolylthio)(m-phenoxyphenyl)-acetonitrile

生成物 1

HCID 13023169alpha-(p-Tolylthio)-alpha-(m-phenoxyphenyl)propionitrile収率 86%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

1.245 g of alpha-(p-tolylthio)(m-phenoxyphenyl)-acetonitrile was dissolved in 5 ml of anhydrous methanol, and a 2.2 M methanol solution of sodium methoxide was added at room temperature in an atmosphere of argon. The mixture was stirred, and 0.35 ml of methyl iodide was added dropwise. The mixture was further stirred for 30 minutes at room temperature. Then, an aqueous solution of ammonium chloride (3 g/20 ml) was added, and the mixture was extracted with 20 ml of ether three times. The extract was washed with 30 ml of water three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel; hexane and methylene chloride) to afford 1.125 g (yield 86%) of alpha-(p-tolylthio)-alpha-(m-phenoxyphenyl)propionitrile as a pale yellow oil.

後処理

  1. stirringThe mixture was further stirred for 30 minutes at room temperature
  2. extractionthe mixture was extracted with 20 ml of ether three times
  3. washThe extract was washed with 30 ml of water three times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe oily residue was purified by column chromatography (silica gel; hexane and methylene chloride)

出典と根拠

ORDレコード
ord-41e3db438f8244859a3e784bcced1f33
出典データセット
uspto-grants-1982_07
特許番号
US04340740

反応ノート

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