Réaction #531879

Équation de réaction

ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate

2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride

triethylamine

→

ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate

Rendement 100.3%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrethe mixture was evaporated
2. 2
   workup.ADDITIONThe residue was diluted with AcOEt
3. 3
   Filtrationthe precipitate was filtered off
4. 4
   AutreThe filtrate was evaporated

Mode opératoire

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.1 g, 0.369 mmol, 1 eq.) in 5 ml of tetrahydrofuran were added 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride (0.106 g, 0.40 mmol, 1.1 eq.) and triethylamine (TEA) (0.112 g, 1.10 mmol, 3 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate (0.170 g, 99% yield).

Source