Chloroacetonitrile → (Phenylthio)acetonitrile

HRID 477308

Reaction equation

HRID 477308 reaction equation
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

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 7969Thiophenol

Product 1

HCID 78891(Phenylthio)acetonitrile

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-780b13dcc76740439d5a650b3e659243
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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