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Method for synthesizing amino biaromatic compound

A technology for synthesizing amino groups and compounds, which is applied in the preparation of amino compounds, the preparation of amino compounds from amines, the preparation of organic compounds, etc., can solve the problems of high cost, long route and high manufacturing cost, and achieve the effect of breaking through novelty

Active Publication Date: 2016-10-05
SHANGHAI XIAOMING DETECTION TECH SERVICE CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014]CN104016915 reported the use of Pd(OH)2 / C as a catalyst, o-acetamidobromobenzene and p-chlorophenylboronic acid carried out Suzuki coupling Reaction synthesizes the method for 4'-chloro-2-acetamidobiphenyl (see reaction formula VI)), although this method has the advantage that catalyst can be recycled and reused, it still needs to use more expensive p-chlorophenylboronic acid; o-acetyl There is no industrial production of aminobromobenzene, and the price of o-bromoaniline for its preparation is as high as 400,000 or more per ton, and it uses acetyl to protect the amino group, and the acetyl group needs to be deprotected to obtain the intermediate for the synthesis of boscalid. Longer, will inevitably lead to high industrial manufacturing costs

Method used

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  • Method for synthesizing amino biaromatic compound
  • Method for synthesizing amino biaromatic compound
  • Method for synthesizing amino biaromatic compound

Examples

Experimental program
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Effect test

Embodiment 1

[0051] Add 6.18 g of potassium o-nitrobenzoate, 0.11 g of cuprous iodide, 0.06 g of palladium acetylacetonate, 0.18 g of o-phenanthroline, 3.80 g of p-chloro Bromobenzene and 40 grams of anhydrous polyethylene glycol PEG-400, then nitrogen vacuum replacement three times, under the protection of nitrogen, stirring

[0052] Raise the temperature to 190 degrees Celsius and react for 24 hours. After detecting the reaction with a gas chromatograph or a liquid chromatograph, the reaction solution was cooled to room temperature, and the reaction solution was extracted 10 times with 40 milliliters of ether. After the extracts were combined, they were washed twice with 200 milliliters of water, and the organic phase was concentrated with a rotary evaporator. The obtained oily mixture was recrystallized with petroleum ether, and after filtration, 3.87 g of yellow-brown 4'-chloro-2-aminobiphenyl was obtained, with a yield of 95% and a purity of 99%. The target compound was characterized...

Embodiment 2

[0054] Add 6.18 g of potassium o-nitrobenzoate, 0.11 g of cuprous iodide, 0.06 g of palladium acetylacetonate, 0.18 g of o-phenanthroline, 3.80 g of p-chloro Bromobenzene and 3A molecular sieves were replaced by nitrogen vacuum three times. Under the protection of nitrogen, 40 grams of anhydrous polyethylene glycol PEG-400 was added, and then replaced by nitrogen vacuum three times. Under the protection of nitrogen, the temperature was raised to 190 degrees Celsius with stirring. Reaction 24 Hour. After detecting the reaction with a gas chromatograph or a liquid chromatograph, the reaction solution was cooled to room temperature, and the reaction solution was extracted 10 times with 40 milliliters of ether. After the extracts were combined, they were washed twice with 200 milliliters of water, and the organic phase was concentrated with a rotary evaporator. The obtained oily mixture was recrystallized with petroleum ether, and after filtration, 3.7 g of yellow-brown 4'-chloro-...

Embodiment 3

[0056] Add 6.18 g of potassium o-nitrobenzoate, 0.11 g of cuprous iodide, 0.06 g of palladium acetylacetonate, 0.18 g of o-phenanthroline, 3.80 g of p-chloro Bromobenzene and 3A molecular sieves were replaced by nitrogen vacuum three times. Under the protection of nitrogen, 40 grams of anhydrous trimethylbenzene was added, and then replaced by nitrogen vacuum three times. Under the protection of nitrogen, the mixture was stirred and heated to 160 degrees Celsius, and reacted for 24 hours. After detecting the end of the reaction with a gas chromatograph or a liquid chromatograph, the reaction solution was cooled to room temperature, added 5 grams of diatomaceous earth and stirred for 5 minutes, then filtered under reduced pressure through a Buchner funnel covered with 3 cm of diatomaceous earth, and washed with ethyl acetate The ester was washed with diatomaceous earth until the filtrate flowing down was colorless and clear. The filtrate was concentrated with a rotary evaporator...

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Abstract

The invention relates to a method for synthesizing an amino biaromatic compound. The method comprises the following steps: reacting a nitroaromatic formic acid compound, an alkali and a solvent, removing water, adding substituted halobenzene, a catalyst and a ligand, and reacting; or reacting prepared dry nitroaromatic formate, substituted halobenzene, the catalyst, the ligand and the solvent; and extracting the obtained reaction product with the solvent, concentrating the obtained extract, and purifying the obtained concentrate to obtain the amino biaromatic compound. Compared with the prior art for synthesizing the amino biaromatic compound through two steps comprising coupling and reducing (such as hydrogenating), the method for synthesizing the amino biaromatic compound from cheap and easily available nitroaromatic formic acid and substituted halobenzene in the high-boiling point solvent under the action of the catalyst through a one-step reaction has the advantages of novel reaction, high safety, high yield, high efficiency, low cost and industrialization realization.

Description

technical field [0001] The invention relates to the field of synthesis of pesticide compounds, in particular to a method for synthesizing aminobiaryl compounds. Background technique [0002] Boscalid is a new type of nicotinamide fungicide discovered by BASF in 1992. The chemical name is 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide. Boscalid kills bacteria It has a wide spectrum and is active against almost all types of fungal diseases. It is very effective in preventing and controlling powdery mildew, gray mold, sclerotinia and various rot diseases, and is also effective against other resistant bacteria. It is mainly used for Including the prevention and control of diseases of rapeseed, grapes, fruit trees, vegetables and field crops. Its mechanism of action transfers in plants through foliage penetration, inhibits mitochondrial succinate dehydrogenase, hinders the tricarboxylic acid cycle, causes amino acid and sugar deficiency, reduces energy, interferes with cell di...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C211/45C07C209/68C07C209/36
Inventor 雷建光赵宏伟
Owner SHANGHAI XIAOMING DETECTION TECH SERVICE CO LTD
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