Preparation method of 1-(2-chloro-4-pyridyl)-3-phenylurea

A pyridine phenyl urea and pyridyl technology are applied in the field of preparation of phenyl urea-type cytokinin efficient plant production regulators pyridine phenyl urea and 1--3-phenyl urea, and can solve the problem of difficult industrialized production and difficult raw materials. It is easy to remove, the preparation period is short, and the operation is simple and convenient.

Inactive Publication Date: 2014-06-25
ZHEJIANG TIDE CROP TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0011] Above-mentioned routes 1 and 2 all need to use phosgene when synthesizing isocyanic acid, and phosgene is not easy to obtain; Route 1 also needs expensive 2-chloro-4-aminopyridine excessive, has caused recovery difficulty, and cost is higher; Route 1 In the reaction process, there is also the production of 1,3-diphenylurea by-product, which makes it difficult to improve the product purity; the raw material of route 3 is not easy to obtain, and there are by-products, which is not easy for industrial production

Method used

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  • Preparation method of 1-(2-chloro-4-pyridyl)-3-phenylurea
  • Preparation method of 1-(2-chloro-4-pyridyl)-3-phenylurea
  • Preparation method of 1-(2-chloro-4-pyridyl)-3-phenylurea

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preparation example Construction

[0034] Its specific preparation method steps are as follows:

[0035] (1) Using 2-chloro-4-aminopyridine and phenyl chloroformate as raw materials, potassium carbonate, sodium carbonate, triethylamine, pyridine, N,N-dimethylaniline, 4-dimethylaminopyridine (DMAP ), N,N-diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane (DABCO), substituted pyridine and other inorganic bases or organic bases are used as acidic agents, Toluene, xylene, chlorobenzene, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dioxane, acetonitrile, ethylene glycol dimethyl ether, One of ethylene glycol diethyl ether, ethyl acetate, acetone, butanone, dichloromethane, and chloroform is used as solvent A; 2-chloro-4-aminopyridine and acid agent are dissolved in solvent A, and then added Phenyl chloroformate, stirred and reacted at -5-80°C, preferably 0-60°C, followed by liquid phase tracking to monitor the completion of the reaction, distilled to a part of the solvent under r...

Synthetic example 1

[0039] (1) Dissolve 38.8g of 2-chloro-4-aminopyridine and 33.5g of triethylamine in 400mL of methyl ethyl ketone, then add phenyl chloroformate, stir the reaction at 40°C, monitor the completion of the reaction by liquid phase tracking, and distill under reduced pressure Part of the solvent was removed, and a white solid was precipitated, which was filtered to obtain 73.2 g of phenyl 2-chloro-pyridine-4-carbamate, with a content of 99%.

[0040] (2) Add 50g of phenyl 2-chloro-pyridine-4-carbamate, 20.5g of aniline, and 2.1g of N,N-diisopropylethylamine into 300mL of tetrahydrofuran (THF) solution, reflux After the reaction was complete, tetrahydrofuran (THF) was distilled under reduced pressure, then an appropriate amount of water was added and stirred for 0.5 hours, and filtered under reduced pressure to obtain 48 g of white solid CPPU with a content of 98.8%.

Synthetic example 2

[0042] (1) Dissolve 38.8g of 2-chloro-4-aminopyridine and 26.3g of pyridine in 400mL of toluene solvent, then add phenyl chloroformate, stir the reaction at 30°C, monitor the completion of the reaction by liquid phase tracking, and distill under reduced pressure Part of the solvent was removed, and a white solid was precipitated, which was filtered to obtain 73.1 g of phenyl 2-chloro-pyridine-4-carbamate, with a content of 99.1%.

[0043] (2) Add 50g of phenyl 2-chloro-pyridine-4-carbamate, 20.5g of aniline, and 2.4g of 4-dimethylaminopyridine (DMAP) to 300ml of N,N-dimethylformaldehyde In the amide (DMF) solution, stir and react at 80°C. After the reaction is complete, add an appropriate amount of water to precipitate a solid, and filter under reduced pressure to obtain 47.88 g of white solid CPPU with a content of 99.0%.

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Abstract

The invention discloses a preparation method of a phenylurea-type cytokinin high-efficiency plant growth regulator pyridyl phenylurea of which the chemical name is 1-(2-chloro-4-pyridyl)-3-phenylurea (also called CPPU), which comprises the following steps: reacting 2-chloro-4-aminopyridine and phenyl chloroformate to obtain phenyl 2-chloropyridyl-4-carbamate, and reacting with aniline to obtain the CPPU. The method has the advantages of accessible raw materials, fewer byproducts, high reaction yield and high product content, is simple to operate, greatly lowers the production cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a crop growth regulator, in particular to a phenylurea-type cytokinin high-efficiency plant production regulator pyridinephenylurea, whose chemical name is 1-(2-chloro-4-pyridyl )-3-phenylurea preparation method. Background technique [0002] A kind of 1-(2-chloro-4-pyridyl)-3-phenylurea (also known as forchlorfenuron, steryou, pyroxuron, CPPU, KT-30 or 4PU-30) of the present invention, its The molecular structure is: [0003] [0004] It is a new type of high-activity plant growth regulator, with high-activity phenylurea cytokinin substances, which can promote plant growth, early maturity, delay the aging of leaves in the later stage of crops, and increase production. Since 1981, the Faculty of Pharmacy, University of Tokyo, Japan Since Okamoto, Shouto and others discovered its high cell division activity, chemists from various countries have carried out in-depth synthesis research and application ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75
CPCC07D213/75
Inventor 郝树林杨征宇李晓东孙钊
Owner ZHEJIANG TIDE CROP TECH
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