Réaction #531885

Équation de réaction

ethylisothiocyanate

3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile

NaH

→

(2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide

Rendement 29.1%

Solvants

dimethyl formamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirring continued overnight
2. 2
   AutreThe reaction was quenched with water
3. 3
   Extractionextracted with AcOEt
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated under vacuum
6. 6
   AutreThe residue was purified by chromatography on silica gel

Mode opératoire

A solution of 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.15 g, 0.606 mmol, 1 eq.) in 2 ml of dimethyl formamide (DMF) was treated with NaH (60% in mineral oil, 0.029 g, 0.727 mmol, 1.2 eq.) and stirring allowed for 1 h. ethylisothiocyanate (0.105 g, 1.21 mmol, 2 eq.) was added and stirring continued overnight. The reaction was quenched with water and extracted with AcOEt. The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide (0.059 g, 27% yield) as a white solid.

Source