Chloroacetonitrile → (Phenylthio)acetonitrile

HRID 477308

반응식

HRID 477308 반응식
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

참가 물질

4

반응물 2

HCID 7856ChloroacetonitrileHCID 7969Thiophenol

생성물 1

HCID 78891(Phenylthio)acetonitrile

시약·촉매·용매 1

HCID 2723922Sodium ethoxide용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-780b13dcc76740439d5a650b3e659243
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886835

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