Reaktion #531885

Reaktionsgleichung

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

Ausbeute 29.1%

Lösungsmittel

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring continued overnight
2. 2
   SonstigeThe reaction was quenched with water
3. 3
   Extraktionextracted with AcOEt
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated under vacuum
6. 6
   SonstigeThe residue was purified by chromatography on silica gel

Vorschrift

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.

Quelle