CS214577B1 - Process for the preparation of 2-chloro-5- [alpha- (3-pentadecylphenoxy) bnthramido] aniline - Google Patents

Abstract

The invention relates to a method of preparing 2-chloro-5-[alpha-(3-pentadecylphenoxy)butyramido]aniline by reducing l-nitro-2-chloro-5-[alpha-(pentadecylphenoxyjbutyramido]benzene with zinc and calcium chloride. This is a new, technologically undemanding and more economical method of preparing an intermediate product for the production of color-forming components characterized by the fact that the reduction is carried out with zinc in of a water-ethanol solution of calcium chloride at 80°C, and the final product is isolated by pouring the filtered reaction mixture onto ice or into cold water, and the excluded product is filtered off with suction.

Description

The invention relates to a process for the preparation of 2-chloro-5- [alpha- (3-pentadecylphenoxy) butyramido] aniline by reducing 1-nitro-2-chloro-5- [alpha (pentadecylphenoxy) butyramido] benzene with zinc and calcium chloride. in

It is a new, technologically undemanding and more economical process for preparing the intermediate for producing coloring agents characterized in that the reduction is carried out by zinc in an aqueous-ethanolic calcium chloride solution at 80 ° C and the final product is isolated by pouring the filtered reaction mixture onto ice or cold water and the precipitated product is filtered off with suction.

The invention relates to a process for the preparation of 2-chloro-5- [alpha- (3-pentadecylphenoxy) butyramido] aniline by reducing 1-nitro-2-chloro-5- [alpha (pentadecylphenoxy) butyramido] benzene with zinc and calcium chloride.

2-Chloro-5- [alpha- (3-pentadecylphenoxy) butyramido] aniline (II) is produced as one of the intermediates for producing colorformers by reducing 1-nitro-2-chloro-5- {alpha- (3-pentadecylphenoxy) J-butyramido of the benzene of formula (I) by iron or zinc in acetic acid or by hydrogenation on a Raney-nickel catalyst.

Brit, Pat. 830, 797 [1958]; Fuji Photo: German Pat. 2,542,651 (1976)]. In the first case, there is a complication in the insulation with ferrous and zinc salts, in the second case it is necessary to work in a pressure equipment.

For

GaCl ₂ EtGM • i

The above-mentioned drawbacks do not have the process according to the invention, which is based on the fact that the reduction of the nitro compound (I) to the amino compound (II) can be carried out by zinc in an aqueous ethanolic solution of calcium chloride. The reaction is carried out at 80 ° C and terminated by heating the reaction mixture to boiling. The product is isolated by pouring the filtered reaction mixture onto ice and suctioning off the precipitate. The product obtained is a white or light brownish substance which is used for further synthesis without further purification. The nitro compound (s) used for the reduction must be free of the starting 2-chloro-5-nitroaniline, which is otherwise reduced to the m-phenylenediamine derivative during the reaction, cannot be practically separated from the main fraction and causes blackening of the product and deterioration.

The advantage of the new 2-chloro preparation process; -5 [alpha- (3-pentadecylphenoxy) -butyramido] aniline is that it is technologically undemanding and economically more advantageous than the hitherto used methods. '’

Example

A three-necked 11-ml flask equipped with a stirrer and a reflux condenser was charged with 340 ml of ethanol, a solution of 35 g of calcium chloride in 100 ml of water and 218 g of dense dust. The mixture is heated to 80 ° C and 242 g of 1-nitro-2-chloro-5- [alpha- (3-pentadecylphenoxy) butyramido] benzene (I) are added slowly and in portions at this temperature. After completion of the reaction, the suspension is suctioned off hot while the unreacted zinc is washed on the filter with 100 ml of hot ethanol, the soldered ethanolic filtrates are poured onto ice, and the precipitate is filtered off with suction and washed with water until neutral. m.p. 70-72 DEG C., yield 213 g, i.e. 93% of theory.

Claims (1)

Object of the invention Preparation of 2-chloro-5-fluoro-alpha- (3-pentadecylphenoxy jbutyramido] aniline of formula ^{II; ··:!} '^ ··>·' St ά · · ^C 15 ^H 31 \ l-nitro-2-diffracted -? - 5- [alpha - (3-pehtadecylphenoxybutyramido) benzene of formula I o ₂ n · Et t NH .CGCH CHO · ^C 15 ^H 31 characterized in that the reduction is carried out by isolation by pouring the filtered reaction mixture of cane, an aqueous-ethanolic chloride solution into ice or cold water and precipitated calcium at 8d ° C and the final product the product is filtered off with suction.