反応 #6036

反応方程式

methyl isothiocyanate

lithium diisopropylamide

4-chlorophenylmethylbenzylcyanide

→

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

収率 31.4%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   その他The solvent was removed from the reaction mixture under reduced pressure and water
4. 4
   workup.ADDITIONwas added to the residue
5. 5
   抽出The mixture was extracted with 50 ml of ethyl acetate
6. 6
   その他dried
7. 7
   その他condensed under reduced pressure
8. 8
   その他purified by silica gel chromatography
9. 9
   その他recrystallized from hexane

実験手順

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.

出典