반응 #6111

ord-b40073ab084446aca3ddff0719ca2133

반응 방정식

N#Cc1ccc(-c2ccc(I)cc2)cc1
4-(4-iodophenyl)benzonitrile
C[S-].[Na+]
sodium thiomethylate
N#Cc1ccc(-c2ccc(S)cc2)cc1
pale yellow solid
수율 106.6%
N#Cc1ccc(-c2ccc(S)cc2)cc1
4-(4-mercaptophenyl)benzonitrile
수율 106.6%

반응 조건

온도
100°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출The expected product is extracted with ethyl acetate
  2. 2
    세척The resulting organic phase is washed with water until the pH of the washings
  3. 3
    건조dried over magnesium sulfate
  4. 4
    기타evaporated under reduced pressure

실험 절차

3.25 g (10.8.10-3 mol) of 4-(4-iodophenyl)benzonitrile are dissolved in 50 ml of hexamethylphosphoramide, and 3.05 g (43.4.10-3 mol) of sodium thiomethylate are then added to the solution. The reaction mixture is heated at 100° C. for 1.5 hours and then, after cooling, hydrolyzed in a 1 N hydrochloric acid/ice mixture. The expected product is extracted with ethyl acetate. The resulting organic phase is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and then evaporated under reduced pressure to give 2.4 g (quantitative yield) of a pale yellow solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05246961uspto-grants-1993_09