Reacción #710487

Ecuación de reacción

N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide

sodium hydroxide

→

N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide

Rendimiento 17.1%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITION1 mL of concentrated bleach was added to the reaction mixture at room temperature
2. 2
   Extracciónwas then extracted twice with diethyl ether
3. 3
   SecadoThe combined organic phases were dried over magnesium sulphate
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   Otroto yield 1.41 g of crude product which
6. 6
   Otrowas purified by chromatography on silica gel with ethyl acetate/heptane (3/7 v/v)
7. 7
   Lavadoas eluting phase

Procedimiento

2.00 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide (Int-5), (known from WO 2004/016088), were dissolved in 20 mL of methanol. 1 mL of concentrated bleach was added to the reaction mixture at room temperature. The reaction mixture was stirred for 24 hours at room temperature. 20 mL of a 1N aqueous solution of sodium hydroxide were added to the reaction mixture which was then extracted twice with diethyl ether. The combined organic phases were dried over magnesium sulphate, concentrated in vacuo to yield 1.41 g of crude product which was purified by chromatography on silica gel with ethyl acetate/heptane (3/7 v/v) as eluting phase. 340 mg (17%) of desired N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were obtained, [M+1]=395.

Fuente