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

HRID 1759421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1759421
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-41e3db438f8244859a3e784bcced1f33
Quelldatensatz
uspto-grants-1982_07
Patentnummer
US04340740

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