Reaction #531885

Reaction equation

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

Yield 29.1%

Solvents

dimethyl formamide

Conditions

Workup

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

Procedure

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