Sodium Cyanide → 2-(3,5-Dimethoxyphenylthio)-benzyl cyanide

HRID 567879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567879
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14]Br)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C-:20]#[N:21].[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][C:20]#[N:21])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 155124432-(3,5-Dimethoxyphenylthio)benzyl bromide

Produkt 1

HCID 109241262-(3,5-Dimethoxyphenylthio)-benzyl cyanideAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-(3,5-Dimethoxyphenylthio)benzyl bromide (9.53 g) was dissolved in dimethyl sulfoxide (90 ml), sodium cyanide (2.77 g) was added thereto and the mixture was stirred at 80° C. for 1.5 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1) to give 2-(3,5-dimethoxyphenylthio)-benzyl cyanide (4.91 g, yield of 61%).

Aufarbeitung

  1. washwashed with water and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-005140692c7c426fa7acaf2cac386e02
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180659B2

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