Reaktion #710487

Reaktionsgleichung

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

Ausbeute 17.1%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle