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Method for preparing closantel sodium intermediate by catalytic hydrogenation

A technology of closantamide sodium and catalytic hydrogenation, which is applied in the field of medicine and chemical industry, can solve the problems of low product yield and product quality, large amount of raw and auxiliary materials, and relatively large pollution impact, and achieve product yield and purity High, short reaction time, simple process effect

Active Publication Date: 2013-12-04
ZHEJIANG RONGYAO CHEM +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the disadvantage of this method is that the operation process is cumbersome, the amount of raw and auxiliary materials is large, and a large amount of scrap iron powder is produced after reduction with iron powder, which is relatively viscous and easy to contain products and impurities. The recovery cost is high, the labor intensity is high, and the environment is harmful. The impact of pollution is greater; and the product yield and product quality are low

Method used

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  • Method for preparing closantel sodium intermediate by catalytic hydrogenation
  • Method for preparing closantel sodium intermediate by catalytic hydrogenation
  • Method for preparing closantel sodium intermediate by catalytic hydrogenation

Examples

Experimental program
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Effect test

Embodiment 1

[0020] In a 500mL stainless steel autoclave, add 4-chloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexadienylidene]phenylacetonitrile 30.5g ( 0.1mol) and Ni-Al type nickel 0.3g, then add 200mL of 95% ethanol, replace with hydrogen 3 times, feed hydrogen, control the system pressure to 0.2MPa, start stirring, heat up, control the reaction temperature at 80°C, and react The system pressure drops gradually until the pressure does not drop within 10 minutes, and the reaction takes about 2 hours. After the reaction is finished, after cooling, filter and recycle the catalyst for use. Collect the filtrate, concentrate under reduced pressure to about 40 mL, recover the solvent, and cool the residue to -5°C to 5°C to precipitate crystals, leave it overnight, filter, and dry to obtain the 4-chlorophenyl-(2-chloro-4 -Amino-5-methylphenyl)cyanomethane 27.8 g. The HPLC purity was 97.5%, and the yield was 93.2%.

Embodiment 2

[0022] In a 500mL stainless steel autoclave, add 4-chloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexadienylidene]phenylacetonitrile 30.5g ( 0.1mol) and Ni-Al type nickel 0.3g, then add 200mL of toluene, replace with hydrogen 3 times, feed hydrogen, and control the system pressure to 2MPa, start stirring, raise the temperature, control the reaction temperature at 100°C, the reaction system pressure Decrease gradually until the pressure does not drop within 10 minutes. The reaction takes about 8 hours. After the reaction is completed, after cooling, filter, recover the catalyst and apply it mechanically, collect the filtrate, concentrate under reduced pressure to about 40mL, recover the solvent, and cool the residue to -5℃~ Crystals were precipitated at 5°C, left overnight, filtered, and dried to obtain 27.2 g of 4-chlorophenyl-(2-chloro-4-amino-5-methylphenyl)cyanomethane. The HPLC purity was 98.2%, and the yield was 91.9%.

Embodiment 3

[0024] In a 500mL stainless steel autoclave, add 4-chloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexadienylidene]phenylacetonitrile 30.5g ( 0.1mol) and Ni-Al type nickel 0.03g, then add 300mL of xylene, first pass through hydrogen for replacement 3 times, then pass through hydrogen, and control the system pressure to 5MPa, start stirring, heat up, and control the reaction temperature at 120°C , the pressure of the reaction system drops gradually until the pressure does not drop within 10 minutes, and the reaction takes about 10 hours. After the reaction is completed, cool, filter, recover the catalyst and apply it, collect the filtrate, concentrate under reduced pressure to about 40mL, recover the solvent, cool the residue to -5°C to 5°C to precipitate crystals, leave it overnight, filter, and dry to obtain 4-chlorobenzene 26.3 g of di-(2-chloro-4-amino-5-methylphenyl)cyanomethane, the HPLC purity was 95.6%, and the yield was 86.5%.

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Abstract

The invention relates to a method for preparing a closantel sodium intermediate by catalytic hydrogenation, belonging to the technical fields of medicine and chemistry. The method comprises the following steps of: adding 4-chlorine-alpha-[2-chloro-4-(isonitroso)-5-methyl-2,5-cyclohexadienylidene] benzyl cyanide (I) and a catalyst into an organic solvent; introducing hydrogen gas; and undergoing a hydrogenated reduction reaction to obtain the closantel sodium intermediate, i.e., 4-chlorphenyl-(2-chloro-4-amino-5-methyl phenyl)methyl cyanide (II). Compared with a ferrous powder reduction method, the method has the advantages of simple process, small dosage of solvent, short reaction time, avoidance of residual iron ions in a product, high product yield and purity; and meanwhile, the catalyst can be used repeatedly, so that the pollution of iron mud is reduced, and the industrialization production is facilitated.

Description

technical field [0001] The present invention relates to a kind of closamide sodium intermediate, in particular to a kind of closantamide sodium intermediate 4-chlorophenyl-(2-chloro-4-amino-5-methylphenyl)cyano A method for preparing methane by catalytic hydrogenation belongs to the technical field of medicine and chemical industry. Background technique [0002] Closantel Sodium (Closantel Sodium) is a strong oxidative phosphorylation uncoupling agent, which can inhibit the phosphorylation process of the mitochondria of parasites. It is a high-efficiency, low-toxic broad-spectrum anthelmintic, which has great development potential in the market. [0003] And 4-chlorophenyl-(2-chloro-4-amino-5-methylphenyl) cyanomethane is a key intermediate for the synthesis of iodosamide sodium. However, there are few reports on the synthesis method of 4-chlorophenyl-(2-chloro-4-amino-5-methylphenyl)cyanomethane in the prior art, mainly the reduction synthesis method of iron powder. For ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/42C07C253/30
Inventor 陈仁尔洪志蒋华江苏为科郑人华
Owner ZHEJIANG RONGYAO CHEM
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