CS255045B1 - N- (2,6-dichlorophenyl) -benziminophenyl ether - Google Patents

Abstract

The solution relates to N-(2,6-dichlorophenyl)-benziminophenyl ether, which serves as an intermediate for the preparation of diclofenac sodium, which is a desired drug with analgesic and anti-inflammatory effects.

Description

which is an intermediate for the preparation of o- (2,6-dichloroanilino) -phenylacetic acid, whose sodium salt (diclofenac sodium) is a widespread drug with an anti-pain and anti-inflammatory effect.

The novel compound of formula (I) is prepared by reacting N- (2,6-dichlorophenyl) -benzimidoyl chloride with an alkali metal phenolate in a protophilic solvent medium (aliphatic ethers or esters of aliphatic acids), between 10 ° and 90 ° C by diluting the reaction mixture with water, separating the organic phase and evaporation of the solvent gave crude N- (2,6-dichlorophenyl) -benziminophenyl ether as a yellow viscous, crystalline oil on standing. Crystallization of the crude product from petroleum ether gave pure N- (2,6-dichlorophenyl) -benziminophenyl ether, purity 99% (determined by gas chromatography), as a yellow crystalline solid, m.p. 70.5 ° to 71.0 ° C.

The following example illustrates the preparation of a compound of the invention but does not limit it.

Example

To a suspension of 13.3 g (0.10 mole) of potassium phenoleate in 20 ml of me255 045 thanol is added, while stirring and cooling in a water bath, a solution of 28.5 g of 0.10 mole of N- (2,6-dichlorophenyl) benzimidoyl chloride in 30 ml of ethyl acetate such that the temperature of the reaction mixture is maintained between 30 and 40 ° C; after the exothermic reaction subsided, the stirred reaction mixture was heated to 50 ° C and maintained at this temperature for 3 hours to produce a pro-reaction of both components. The reaction mixture, cooled to room temperature, was diluted with 70 ml of ethyl acetate and shaken with dest. water (β x 30 ml) leaves inorganic salts and unreacted potassium phenolate residues; the organic phase, dried over sodium sulfate, is freed from the solvent by distillation under reduced pressure. 25.0 g, i.e. 73.0% of th, is obtained. an oily product which gradually crystallizes on standing. Crystallization from hexane gave 20 g of N (2,6-dichlorophenyl) -benziminophenyl ether of purity 98.5% as a yellow crystalline solid, m.p. 70.5 ° -71 ° C.

Claims (1)

SUBJECT OF THE INVENTION A N- (2,6-dichlorophenyl) -benziminophenyl ether of formula I AND Printed by Moravian printing works, center. 11 100, the class of People's Militia 3, Olomouc Price: 2,40 Kčs