Chloroacetonitrile → (Phenylthio)acetonitrile

HRID 477308

Reaktionsgleichung

Reaktionsgleichung von HRID 477308
Cl[CH2:2][C:3]#[N:4].[C:5]1([SH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CC[O-].[Na+]>[C:5]1([S:11][CH2:2][C:3]#[N:4])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 7856ChloroacetonitrileHCID 7969Thiophenol

Produkt 1

HCID 78891(Phenylthio)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2723922Sodium ethoxideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Chloroacetonitrile (11.4 cc) is added at a temperature in the region of 5° C., in the course of 45 minutes, to a stirred solution of thiophenol (20 g) and a 2M ethanolic solution of sodium ethylate (90 cc). Stirring is maintained for 5 hours at a temperature in the region of 20° C. The reaction mixture is filtered, and the filtrate is evaporated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa). The residue is dissolved in a mixture (30 cc) of cyclohexane and ethyl acetate (70:30 by volume) and the solution is poured onto silica (1,000 g) contained in a column 6.5 cm in diameter. Elution is performed with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent. Phenylthioacetonitrile (14.5 g) is obtained, and is used in the crude state in the subsequent phases.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa)
  3. dissolutionThe residue is dissolved in a mixture (30 cc) of cyclohexane and ethyl acetate (70:30 by volume)
  4. additionthe solution is poured onto silica (1,000 g)
  5. washElution
  6. additionis performed with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-780b13dcc76740439d5a650b3e659243
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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