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Synthetic method of 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide

A synthetic method, the technology of chlorinated biphenyls, applied in the direction of organic chemistry, etc., can solve the problems of expensive raw materials, etc., and achieve the effects of mild reaction conditions, cost reduction, and simple process

Active Publication Date: 2015-06-24
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This route still has the disadvantage of expensive raw materials

Method used

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  • Synthetic method of 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide
  • Synthetic method of 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide

Examples

Experimental program
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Effect test

Embodiment 1

[0027] (1) Add 4.7g (0.03mol) of o-chloronitrobenzene, 3.6g (0.09mol) of sodium hydroxide and 30mL of n-hexane into a 100mL three-necked flask under nitrogen protection, add 0.021g (0.00003mol) of bis( Triphenylphosphine)palladium dichloride, heated up to 50°C, and added dropwise a 30mL n-hexane solution containing 7.0g (0.045mol) of 4-chlorophenylboronic acid. After cooling to room temperature, filter, wash with water until neutral, concentrate, and recrystallize from petroleum ether to obtain 6.3 g of 4'-chloro-2-nitrobiphenyl with a yield of 89.9% and a melting point of 62°C. 1 H NMR (CDCl 3 ), δ: 7.26 (2H, dm, ArH), 7.41 (3H, dm, ArH), 7.51 (1H, dm, ArH), 7.63 (1H, dm, ArH), 7.88 (1H, dd, ArH). MS (m / z): 233 (M + ), 198 (M + -Cl).

[0028] (2) Add 7.0 (0.03mol) g4'-chloro-2-nitrobiphenyl, 8.4g (0.15mol) reduced iron powder, 2.6g (0.045mol) ammonium chloride, 50mL methanol and 10mL water into a 100mL three-necked flask 3.6 g (0.06 mol) of glacial acetic acid was added ...

Embodiment 2

[0032] (1) Under the protection of nitrogen, add 4.7g (0.03mol) o-chloronitrobenzene, 6.7g (0.06mol) potassium tert-butoxide and 30mL chloroform into a 100mL three-necked flask, stir for 10min and then add 0.63g (0.0009mol) bis( Triphenylphosphine)palladium dichloride, heated up to 50°C, and added dropwise a 30mL chloroform solution containing 4.7g (0.03mol) of 4-chlorophenylboronic acid. After cooling to room temperature, filter, wash with water until neutral, concentrate, and recrystallize from petroleum ether to obtain 5.8 g of 4'-chloro-2-nitrobiphenyl with a yield of 82.8%.

[0033](2) Add 7.0 (0.03mol) g4'-chloro-2-nitrobiphenyl, 3.4g (0.06mol) reduced iron powder, 1.8g (0.03mol) ammonium chloride, 50mL ethanol and 10mL water into a 100mL three-necked flask 3.6 g (0.06 mol) of glacial acetic acid was added dropwise at 40° C., and after the addition, the temperature was raised to reflux for 5 h. After cooling to room temperature, filter, concentrate, dissolve with ethyl ...

Embodiment 3

[0037] (1) Add 4.7g (0.03mol) of o-chloronitrobenzene, 3.6g (0.09mol) of sodium hydroxide and 30mL of toluene into a 100mL three-necked flask under nitrogen protection, and add 0.011g (0.000015mol) of bis(tri Phenylphosphine)palladium dichloride, the temperature was raised to 50°C, and a 30mL toluene solution containing 9.4g (0.06mol) 4-chlorophenylboronic acid was added dropwise. After the dropwise addition, the temperature was raised to reflux and kept for 6h. After cooling to room temperature, filter, wash with water until neutral, concentrate, and recrystallize from petroleum ether to obtain 5.0 g of 4'-chloro-2-nitrobiphenyl with a yield of 71.4%.

[0038] (2) Add 7.0 (0.03mol) g4'-chloro-2-nitrobiphenyl, 16.8g (0.3mol) reduced iron powder, 3.5g (0.06mol) ammonium chloride, 50mL ethanol and 10mL water into a 100mL three-necked flask 2.0 g (0.03 mol) of glacial acetic acid was added dropwise at 40° C., and after the addition, the temperature was raised to reflux for 5 h. ...

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Abstract

The invention discloses a synthetic method of 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide. The method comprises the following steps: by taking o-chloronitrobenzene and 4-chlorobenzene boric acid as raw materials, performing Suzuki coupling reaction to generate a intermediate 4'-chloro-2-nitryldiphenyl; subsequently reducing to generate a intermediate 4'-chloro-2-aminodiphenyl; finally condensing the intermediate 4'-chloro-2-nitryldiphenyl and the intermediate 4'-chloro-2-aminodiphenyl with 2-chloronicotinoyl chloride to obtain a target product 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide. The method is used for preparing the 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide and has the advantages of mild reaction condition, simple process, low cost, high yield and the like.

Description

technical field [0001] The present invention relates to a kind of synthetic method of agricultural fungicide, specifically, the present invention relates to a kind of synthetic method of 2-chloro-N-(4'-chlorobiphenyl-2-yl) nicotinamide (boscalid) . technical background [0002] 2-Chloro-N-(4'-chlorobiphenyl-2-yl) nicotinamide (boscalid) is a new type of nicotinamide systemic fungicide developed by BASF, Germany. It has a wide bactericidal spectrum and can be widely used In rapeseed, grapes, fruit trees, vegetables and field crops, it can prevent powdery mildew, gray mold, sclerotinia and various rot diseases. [0003] At present, domestic control of Botrytis cinerea is still dominated by chemical control, mainly using carbendazim and benomyl. Due to the continuous use of benzimidazoles, Botrytis cinerea has developed serious resistance to benzimidazoles. Boscalid is an inhibitor of succinate coenzyme Q reductase in the mitochondrial respiratory chain. It acts on the intra...

Claims

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Application Information

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IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 黄晓瑛王列平宁斌科魏乐毛明珍何琦文张建功苏天铎陈涛张晓光徐泽刚
Owner XIAN MODERN CHEM RES INST
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