반응 #72553

반응 방정식

triethylamine

ethyl(methylsulphanyl)acetate

4-amino-benzonitrile

tBuOCl

→

title product

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

용매

Water

DCM

DCM

DCM

반응 조건

후처리

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
   기타the phases are then separated
4. 4
   세척The organic phase is washed with water
5. 5
   건조The organic phase is dried over sodium sulphate
6. 6
   여과filtered
7. 7
   기타evaporated to dryness
8. 8
   workup.ADDITIONaq. 2M HCl solution is added
9. 9
   workup.STIRRINGAfter stirring overnight
10. 10
    여과the yellow precipitate is filtered off
11. 11
    기타dried in vacuo

실험 절차

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.

출처