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Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile

A technology of nitrophenylacetonitrile and chlorophenylacetonitrile, which is applied in the field of preparation of anticoccidial intermediate 2,6-dichloro-α--4-nitrophenylacetonitrile, which can solve the problem of 4-position chlorine being substituted Low cost, difficult to complete condensation, high cost, etc., to achieve high industrial production value, avoid isomers, and low cost

Active Publication Date: 2013-02-06
江苏中丽新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In order to overcome the disadvantages of high preparation cost of raw material 3,4,5-trichloronitrobenzene, serious three wastes, low activity of substituted chlorine at the 4-position and difficulty in complete condensation in the existing technology, the present invention provides a relatively A low-cost preparation method of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile

Method used

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  • Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile
  • Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile
  • Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Get 50g of distillation residue of 2,4-dichloro-3-fluoronitrobenzene production process (3,5-dichloro-4-fluoronitrobenzene content 87.7%, 2,4-dichloro-3-fluoronitrobenzene The content of benzene is 9.6%, and the content of other impurities is 2.3%. It comes from a dark brown distillation residue with batch number LH20111223 of an enterprise in Linhai, Zhejiang Province in 2011) and is heated and dissolved in 200mL of petroleum ether. Remove the solvent, recrystallize with methanol, filter, wash with cold methanol, and dry in vacuo to obtain 3,5-dichloro-4-fluoronitrobenzene with a content of 98.3% and a yield of 77%.

[0025] Take 21.0g (0.1mol) of 3,5-dichloro-4-fluoronitrobenzene obtained above, 70g of sodium hydroxide dissolved in 70mL of water to make 50% liquid caustic soda, 3g of benzyltriethylammonium chloride and 140mL In tetrahydrofuran, add dropwise a solution of 17.0g p-chlorophenylacetonitrile in 50mL THF at 30°C, heat up to 50°C for 6 hours after dropping, ...

Embodiment 2

[0027]Take 2,4-dichloro-3-fluoronitrobenzene distillation residue 50g (3,5-dichloro-4-fluoronitrobenzene content 86.5%, 2,4-dichloro-3-fluoronitrobenzene The content of benzene is 10.1%, and the content of other impurities is 1.2%, which is derived from the taupe distillation residue with batch number KH20120211 of a company in Kaihua, Zhejiang Province in 2012). The solvent was distilled off, recrystallized with absolute ethanol, filtered, washed with cold ethanol, and dried in vacuum to obtain 3,5-dichloro-4-fluoronitrobenzene with a content of 98.4% and a yield of 75%.

[0028] Take 21.0g (0.1mol) of 3,5-dichloro-4-fluoronitrobenzene obtained as above, 50% liquid caustic soda prepared by dissolving 60g of sodium hydroxide in 60mL of water, 3g of tetrabutylammonium bromide and 120mL of tetrahydrofuran, Add dropwise a solution of 17.0g p-chlorophenylacetonitrile in 50mL tetrahydrofuran at 40°C, heat up to 60°C for 4 hours after dropping, pour the mixture into crushed ice, aci...

Embodiment 3

[0030] Get 50g of distillation residue of 2,4-dichloro-3-fluoronitrobenzene production process (3,5-dichloro-4-fluoronitrobenzene content 84.3%, 2,4-dichloro-3-fluoronitrobenzene The content of benzene is 12.4%, and the content of other impurities is 2.7%. It comes from a dark brown distillation residue with batch number QZ20120324 of a company in Quzhou, Zhejiang Province in 2012) and is heated and dissolved in 260mL of toluene. The solvent was recrystallized once with isopropanol and methanol respectively, and vacuum-dried to obtain 3,5-dichloro-4-fluoronitrobenzene with a content of 98.5% and a yield of 72%.

[0031] Take 21.0g (0.1mol) of 3,5-dichloro-4-fluoronitrobenzene obtained above, 70g of sodium hydroxide dissolved in 70mL of water to make 50% liquid caustic soda, 3g of benzyltriethylammonium chloride and 140mL Add dropwise a solution of 17.0g p-chlorophenylacetonitrile in 50mL tetrahydrofuran to THF at 30°C, heat up to 50°C and react for 6h after dropping, pour the ...

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Abstract

The invention discloses a method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile by condensation of 3,5-dichloro-4-fluronitrobenzene and p-chloro-phenylacetonitrile, wherein the used raw material 3,5-dichloro-4-fluronitrobenzene is derived from distillation residue of a production process for preparing 2,4-dichloro-3-fluronitrobenzene by nitrifying 2,6-dichlor fluorbenzene; and the residue contains 83.5-88.2% of 3,5-dichloro-4-fluronitrobenzene and 9.0-13.3% of 2,4-dichloro-3-fluronitrobenzene, and 3,5-dichloro-4-fluronitrobenzene with content more than 98% can be obtained by selective solvent extraction and once or twice recrystallization and is subjected to condensation with p-chloro-phenylacetonitrile to obtain 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile with yield above 98%. Compared with the existing method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile, the method has the characteristics of inexpensive and easily available raw materials, sufficient utilization of resources, mild conditions, high yield, low wastewater discharge and the like, and is more suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of anticoccidiostat intermediate 2,6-dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile. Background technique [0002] Diclazuril is a chemically synthesized high-efficiency anticoccidial drug developed by the Belgian Janssen Company in the 1980s and first launched in Europe in 1992, with a content of only 1 / 10 6 The mixed feed can completely kill the infected coccidia. It is one of the anticoccidial drugs with the lowest dosage. It has the characteristics of safety, low toxicity and no residue. It has been registered and used in most countries in the world. [0003] [0004] [0005] 2,6-Dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile is an important intermediate in the synthesis of the anticoccidial drug diclazuril. Regarding the synthesis of this intermediate, there is only one method reported in the literature (such as European patent EP0170316), that is, using 3,4,5-trichloronitrobenzene ...

Claims

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Application Information

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IPC IPC(8): C07C255/35C07C253/30
Inventor 郑土才吕延文吾国强
Owner 江苏中丽新材料有限公司
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