Réaction #710487

Équation de réaction

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

Rendement 17.1%

Solvants

methanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source