Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Preparation method of amicarbazone

A technology of amfentrazone and amino, which is applied in the field of preparation of amfentrazone, can solve the problems of poor reaction selectivity, unsatisfactory reaction results, low boiling point of methyl acetate, etc., and achieves mild reaction conditions and strong reaction operability Effect

Pending Publication Date: 2021-12-28
北京怡力生物科技有限公司 +1
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Unfortunately, the method provided by the above-mentioned patents has been tested many times, and the reaction results are not ideal, showing low reaction conversion rate and poor reaction selectivity
If other solvents such as acetone, tetrahydrofuran, ethylene glycol dimethyl ether, acetonitrile, etc. are used instead of methyl acetate as the reaction medium, the reaction results are not ideal
In addition, the above reactions are usually carried out under anhydrous conditions. Methyl acetate has a low boiling point and is easily hydrolyzed, which is difficult to recover in industry, thereby increasing production costs and not being conducive to environmental protection.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of amicarbazone

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0018] The invention provides a method for the preparation of amifentrazone, which comprises, under the catalysis of lithium hydroxide, 3-isopropyl-4-amino-1,2,4-triazolin-5-one (compound II ) and tert-butyl isocyanate (compound III) react chemically in acetonitrile to obtain the target product amenzazone. The reaction is characterized by high selectivity and high yield.

[0019] The applicant found that the lithium chloride in the composite catalyst reported in the patent US5708184 is almost insoluble in solvents such as methyl acetate, acetone, tetrahydrofuran, ethylene glycol dimethyl ether, and acetonitrile. Therefore, lithium chloride cannot effectively coordinate with the reaction substrate, resulting in poor reaction selectivity. Surprising discovery is, when using the lithium hydroxide of catalytic amount instead as catalyzer, when adopting acetonitrile as reaction medium simultaneously, compound (II) and compound (III) can take place chemical reaction smoothly, and t...

Embodiment 1

[0028] Under the protection of nitrogen flow, 360.00g of acetonitrile, 57.29g (0.575mol) of tert-butyl isocyanate, 0.71g (0.030mol) of powdered lithium hydroxide and 71.80g (0.500mol) of 3-isocyanate were successively put into the reaction flask. Propyl-4-amino-1,2,4-triazolin-5-one. Start stirring, heat up to 60° C., and keep the temperature for 60 minutes to complete the reaction. 6.00 g of acetic acid was added to neutralize the alkali in the reaction system, and samples were taken for high-performance liquid chromatography (HPLC) analysis. The reaction conversion rate was 97.9%, and the reaction selectivity was 98.2%.

[0029] After concentration and precipitation under negative pressure, 175ml of water was added, stirred, cooled to 10°C, and filtered. The filter cake was dried to obtain 116.19 g of amenzazone in the form of a white powdery solid with a purity of 97.6% and a yield of 94.0%.

Embodiment 2

[0031] Under the protection of nitrogen flow, 360.00g of acetonitrile, 0.71g (0.030mol) of powdered lithium hydroxide and 71.80g (0.500mol) of 3-isopropyl-4-amino-1,2,4- Triazolin-5-one. Start stirring, raise the temperature to 60° C., drop 57.29 g (0.575 mol) tert-butyl isocyanate into the reaction solution within 30 minutes, and then keep the temperature for 60 minutes. After the reaction was completed, 6.00 g of acetic acid was added to neutralize the alkali in the reaction system, and samples were taken for HPLC analysis. The reaction conversion rate was 97.8%, and the reaction selectivity was 98.7%.

[0032] After concentration and precipitation under negative pressure, 175ml of water was added, stirred, cooled to 10°C, and filtered. The filter cake was dried to obtain 116.78 g of amentrazone in the form of a white powdery solid with a purity of 97.7% and a yield of 94.6%.

[0033] The reactant and consumption of embodiment 1 and 2 are identical, and difference is only ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of organic synthesis, and discloses a preparation method of amicarbazone, and amicarbazone has a structure as shown in a formula (I) in the specification. The method comprises the following steps: carrying out chemical reaction on 3-isopropyl-4-amino-1, 2, 4-triazoline-5-ketone and tert-butyl isocyanate in an acetonitrile medium under the catalytic action of lithium hydroxide, and converting the 3-isopropyl-4-amino-1, 2, 4-triazoline-5-ketone and the tert-butyl isocyanate into the target product amicarbazone with high selectivity and high yield. The method has the advantages of mild reaction conditions, strong reaction operability and no strict requirements on the charging sequence, and is especially suitable for industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of organic molecule synthesis, and in particular relates to a method for preparing amfentrazone. Background technique [0002] Amicarbazone is a triazolinone herbicide discovered by Bayer in 1988 and launched at the World Plant Protection Congress in Brighton, UK in 1999. Amfentrazone is a photosynthesis inhibitor, which is mainly absorbed through roots and leaves, and can effectively control various annual broad-leaved weeds and annual grass weeds that grow in corn fields, sugarcane fields, sugar beet fields, and lawns. The biggest advantage of amfentrazone is that it is safe for groundwater, safe for subsequent crops, and takes a long time for weeding. It is considered to be the best choice to replace the environmentally unfriendly herbicide atrazine. [0003] Bayer company reported a kind of synthetic method of amfentrazone in the patent US5708184, and this method uses the lithium chloride of catalytic a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 王文军吴少祥李静张金萍刘伟
Owner 北京怡力生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com