Synthesis method of intermediate 4'-chloro-2-aminobiphenyl of boscalid

A technology of boscalid and aminobiphenyl, applied in the field of pesticides, can solve the problems of high cost of raw materials, complicated process, poor operability, etc., and achieve the effect of easy-to-obtain raw materials, simple process flow, and reduce material transfer loss

Active Publication Date: 2017-02-01
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The purpose of the present invention is to provide a novel process for synthesizing 4'-chloro-2-aminobiphenyl, which solves the problems of complex traditional process, poor operability and high raw material cost of boscalid intermediates, and realizes real simplification Process flow, reduce raw material cost, clean process

Method used

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  • Synthesis method of intermediate 4'-chloro-2-aminobiphenyl of boscalid

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Add p-chloroaniline (3.86g, 0.03mol), 5.8g water, 12mL hydrochloric acid in a 250mL four-neck round bottom flask, adjust the system temperature to 50-70°C, then cool down to 0-5°C, and add sodium nitrite ( 2.26g, 0.033mol) in aqueous solution. The reaction is about 2h to produce the diazonium salt. The yield measured by acid titration (calculated as p-chloroaniline) was 97.5%. Under nitrogen protection, the above diazonium salt was cooled to -13°C, and sodium hydroxide solution (23.5ml, 8mol / L) was added dropwise to prepare diazonium salt lye. Aniline (28g, 0.3mol), 5ml of water, heated to 70°C, added the lye solution of the above-mentioned diazonium salt into the system dropwise, and added dropwise for 2 hours, and detected 0.2% of the remaining diazonium salt, and the vacuum was above 0.095Mpa, and the 20g of aniline and 9g of water, add 20ml of toluene to the bottom liquid, pass through hydrochloric acid gas, continue to stir, after fully separated, cool to -5-0°C ...

Embodiment 2

[0034] Add p-chloroaniline (3.86g, 0.03mol), 6g water, 10mL hydrochloric acid in a 250mL four-neck round bottom flask, adjust the system temperature to 50-70°C, then cool to 0-5°C, add sodium nitrite (2.2 g, 0.032mol) in aqueous solution. The reaction is about 2h to produce the diazonium salt. The yield measured by acid titration (calculated as p-chloroaniline) was 97.2%. Under nitrogen protection, the above diazonium salt was cooled to -15°C, and sodium hydroxide solution (25ml, 8mol / L) was added dropwise to prepare diazonium salt lye. Aniline (25.11g, 0.27mol), 10ml THF, heated to 60°C, added the lye solution of the above-mentioned diazonium salt into the system dropwise, and added dropwise for 2 hours, and detected that 0.2% of the diazonium salt was left, the vacuum was above 0.095Mpa, and the 19.5g of aniline and 11g of water, add 25ml of toluene to the bottom liquid, pass through hydrochloric acid gas, continue to stir, after fully separated, cool down to -5-0°C to coo...

Embodiment 3

[0036] Add p-chloroaniline (3.86g, 0.03mol), 6g water, 13mL hydrochloric acid in a 250mL four-neck round bottom flask, adjust the system temperature to 50-70°C, then cool to 0-5°C, add sodium nitrite (2.24 g, 0.0324mol) in water solution. The reaction is about 2h to produce the diazonium salt. The yield measured by acid titration (calculated as p-chloroaniline) was 97.6%. Under the protection of argon, the above-mentioned diazonium salt was cooled to -18°C, and sodium hydroxide solution (24ml, 8mol / L) was added dropwise to prepare a lye solution of the diazonium salt. Aniline (23.25g, 0.25mol), 10ml of DMF, heated to 85°C, dropwise added the lye solution of the above-mentioned diazonium salt into the system, and added dropwise for 2 hours, detected 0.2% of the remaining diazonium salt, and the vacuum was above 0.095Mpa, and the 18g of aniline and 7.6g of water, add 20ml of ethanol to the bottom solution, pass through hydrochloric acid gas, continue to stir, after full separa...

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Abstract

The invention belongs to the technical field of pesticides, and relates to a preparation technology of an intermediate of an agricultural bactericide, in particular to a preparation technology of 4'-chloro-2-aminobiphenyl. The preparation technology uses p-chloroaniline and aniline as raw materials, at least comprises a diazotization reaction, alkalization, a Gomberg-Buckman reaction and a post-treatment process, and is characterized by comprising the following specific steps: under the action of sodium nitrite, performing the diazotization reaction on the p-chloroaniline, water and hydrochloric acid to generate diazonium salt; with water, tetrahydrofuran or DMF and a mixed solvent thereof as a solvent, performing the Gomberg-Buckman reaction on the diazonium salt and the aniline under an alkaline condition so as to achieve synthesis of a key intermediate 4'-chloro-2-aminobiphenyl of boscalid and a structural analogue thereof. Through inflation of hydrochloric acid gas, 4'-chloro-2-aminobiphenyl hydrochloride is obtained; by virtue of recrystallization, purification of the intermediate is achieved; mother liquor is continuously used, and the total yield reaches 80% or higher.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of pesticides, and relates to the preparation technology of agricultural fungicide intermediates, in particular to the preparation technology of 4'-chloro-2-aminobiphenyl. [0003] Background technique: [0004] It is used as a pesticide intermediate in agriculture and is an important intermediate for the manufacture of boscalid. [0005] Molecular formula: C12H10ClN [0006] Chemical name: 2-(4-Chlorophenyl)aniline [0007] English name: 4'-Chloro-Biphenyl-2-Ylamine [0008] Relative molecular mass (according to the international relative atomic mass in 2005): 203.6675 [0009] Structural formula: [0010] [0011] Boscalid is a new type of nicotinamide systemic fungicide developed by BASF, Germany. It is an inhibitor of succinate coenzyme Q reductase in the mitochondrial respiratory chain. It mainly controls many diseases such as powdery mildew, gray mold, sclerotinia, brown rot and root rot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/52
CPCC07C209/68C07C245/20C07C211/52
Inventor 宫薇薇逄廷超邢亮张华曹同波王建刚
Owner JINGBO AGROCHEM TECH CO LTD
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