Chloroacetonitrile → (Phenylthio)acetonitrile

HRID 1074029

反応式

HRID 1074029 の反応式
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

参加物

4

反応物 2

HCID 7856ChloroacetonitrileHCID 7969Thiophenol

生成物 1

HCID 78891(Phenylthio)acetonitrile

試薬・触媒・溶媒 1

HCID 2723922Sodium ethoxide溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0df9754b0b7a48b885c44e9bf37cce9a
出典データセット
uspto-grants-1990_11
特許番号
US04971979

関連ノート

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