Reaction #710487

Reaction equation

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

Yield 17.1%

Solvents

methanol

Conditions

Workup

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
   DryingThe combined organic phases were dried over magnesium sulphate
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Otherto yield 1.41 g of crude product which
6. 6
   Otherwas purified by chromatography on silica gel with ethyl acetate/heptane (3/7 v/v)
7. 7
   Washas eluting phase

Procedure

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