반응 #6036

반응 방정식

methyl isothiocyanate

lithium diisopropylamide

4-chlorophenylmethylbenzylcyanide

→

N-methyl-2-(4-chlorophenyl)-2-cyano-thiopropionamide

수율 31.4%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   기타The solvent was removed from the reaction mixture under reduced pressure and water
4. 4
   workup.ADDITIONwas added to the residue
5. 5
   추출The mixture was extracted with 50 ml of ethyl acetate
6. 6
   기타dried
7. 7
   기타condensed under reduced pressure
8. 8
   기타purified by silica gel chromatography
9. 9
   기타recrystallized from hexane

실험 절차

To a 10 ml tetrahydrofuran solution containing 1.00 g (6 mmole) of 4-chlorophenylmethylbenzylcyanide was added a 3.2 ml tetrahydrofuran solution containing 2 M of lithium diisopropylamide at -60° C. After stirring for 30 minutes under the same conditions, a 5 ml tetrahydrofuran solution containing 0.44 g (6 mmol) of methyl isothiocyanate was added to the mixture and the mixture was allowed to stand at room temperature overnight. The solvent was removed from the reaction mixture under reduced pressure and water was added to the residue. The mixture was extracted with 50 ml of ethyl acetate, dried and condensed under reduced pressure, and then purified by silica gel chromatography and recrystallized from hexane to obtain 0.45 g (yield: 31.4 %) of N-methyl-2-(4-chlorophenyl)-2-cyano-thiopropionamide.

출처