反応 #72553

反応方程式

triethylamine

ethyl(methylsulphanyl)acetate

4-amino-benzonitrile

tBuOCl

→

title product

3-Methylsulphanyl-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

溶媒

Water

DCM

DCM

DCM

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise to the reaction mixture
2. 2
   workup.STIRRINGThe reaction mixture is stirred at ambient temperature for one hour
3. 3
   その他the phases are then separated
4. 4
   洗浄The organic phase is washed with water
5. 5
   乾燥The organic phase is dried over sodium sulphate
6. 6
   ろ過filtered
7. 7
   その他evaporated to dryness
8. 8
   workup.ADDITIONaq. 2M HCl solution is added
9. 9
   workup.STIRRINGAfter stirring overnight
10. 10
    ろ過the yellow precipitate is filtered off
11. 11
    その他dried in vacuo

実験手順

To a solution of 4-amino-benzonitrile (84.64 mmoles) in DCM (200 ml) under a nitrogen atmosphere, at −78° C., there is added, dropwise, tBuOCl (84.64 mmoles) dissolved in 20 ml of DCM and then, after 10 minutes, ethyl(methylsulphanyl)acetate (84.64 mmoles) dissolved in 20 ml of DCM is added dropwise to the reaction mixture. After stirring for one hour at −78° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is stirred at ambient temperature for one hour. Water is added and the phases are then separated. The organic phase is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The residue is taken up in ethyl ether and aq. 2M HCl solution is added. After stirring overnight, the yellow precipitate is filtered off and dried in vacuo to yield the title product, which is used directly in the next reaction.

出典