Preparation method for cycloxylidin enantiomer with photoactivity

A technology of enantiomers and epoxy morphine, which is applied in the field of asymmetric catalytic synthesis of optically active drugs, to achieve the effects of reducing pollution, avoiding self-polymerization, and reducing energy consumption

Inactive Publication Date: 2016-04-13
安徽千和新材料科技发展有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Optically active chiral compounds have important applications in the fields of medicine, pesticides, materials, spices and food, and the value of optically active chiral compounds is much higher than that of their racemic products. Epoxyline products are used as For chiral compounds that can be separated and transformed, it is necessary to study the synthesis and separation of their left-handed (-) and right-handed (+) enantiomers, their pharmacological properties and insecticidal activity, as well as possible toxicity or environmental pollution.

Method used

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  • Preparation method for cycloxylidin enantiomer with photoactivity
  • Preparation method for cycloxylidin enantiomer with photoactivity
  • Preparation method for cycloxylidin enantiomer with photoactivity

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Embodiment 1

[0023] Example 1: The specific preparation method of the enantiomer of 1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine provided by the present invention is as follows:

[0024] (1): Preparation of 1-allyl-N-nitroimidazolidin-2-ylamine:

[0025] Under the protection of nitrogen, 6.5g (0.05mol) of N-nitroiminoimidazolidine was added to 50mL of N,N'-dimethylformamide, stirred for 30 minutes to dissolve it completely, and 2.4g Sodium hydride was added in 3-5 times, and the stirring was continued for about 1 h to obtain a homogeneous light yellow solution. Slowly add 4.9mL (0.06mol) of chloropropene into the above solution with a constant pressure dropping funnel, and then slowly raise the temperature to 40°C after the dropwise addition, TLC or HPLC method is used to monitor the reaction process until the reaction is complete. Suction filtration through diatomaceous earth to remove the inorganic salts produced during the reaction to obtain a yellow transparent solution, which wa...

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Abstract

The invention discloses a preparation method for a cycloxylidin enantiomer with photoactivity, which belongs to the technical field of asymmetric catalytic synthesis of medicines with optical activity. The method comprises a first step of synthesizing 1-allyl-N-2-nitroiminoimidazolidine and a second step of synthesizing the 1-(1,2-glycidyl)-N-2-nitroiminoimidazolidine enantiomer. The method employs sodium hydride to effectively completely remove hydrogen with weak acidity in a resonance structure of N-nitroiminoimidazolidine and convert the hydrogen into a sodium salt, wherein organic by-products are not produced; through asymmetric epoxidation, levorgyrate or dextrorotary enantiomer products with high yield can be obtained; and the method prepares high-purity enantiomer products, substantially improves insecticidal activity of the products and reduces environmental pollution.

Description

technical field [0001] The invention belongs to the technical field of asymmetric catalytic synthesis of optically active drugs, and specifically relates to the synthesis of 1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine (i.e. epoxyline) enantiomers Preparation. Background technique [0002] Epoxyprid is a high-efficiency and low-toxicity insecticide developed on the basis of the common insecticide imidacloprid. It has been gradually promoted in cucumbers, cotton and other crops. It is the best substitute for organophosphorus and organochlorine insecticides. Variety. But at present, what the main synthesis and production technique obtains is the racemate product of epoxyline (see Chinese patent CN101503406A), if this racemate can be split into left-handed (-) and right-handed (+) products, Then the medicinal effect of the optically active enantiomer product will be better, but the cost of dismantling the racemate in industry is very high, and it is difficult to realize ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06
CPCC07B2200/07C07D405/06
Inventor 张千峰夏佳美徐文芳范芳芳
Owner 安徽千和新材料科技发展有限公司
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