Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for synthesizing 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one

A technology based on tert-butyl and methylthio is applied in the field of synthesis of triazinone herbicides, which can solve the problems of difficult control of production risks, difficult procurement of raw materials, poor product quality, etc., and achieve good application prospects, low price, The effect of reducing the production cycle

Active Publication Date: 2013-09-25
苏州诚和医药化学有限公司
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to provide a synthetic 4-amino-6-tert-butyl- 3-Methylthio-1,2,4-triazin-5(4H)-one method

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Acetone 400mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 150g (0.75mol), anhydrous sodium carbonate 119.25g (1.125mol), Add 1 g of potassium iodide into a 1000 mL four-necked reaction flask, slowly add 94.5 g (0.75 mol) of dimethyl sulfate dropwise at a controlled temperature of 25 to 30 ° C under stirring conditions, and after the addition is complete, keep the reaction at 25 to 30 ° C for 3 hours. At the end of the heat preservation reaction, the acetone was evaporated by vacuum concentration, and the acetone was recovered, and then 600mL of water was added, stirred rapidly, separated by suction filtration, and vacuum-dried at 60°C to obtain 4-amino-6-tert-butyl-3-methylthio-1, 2,4-Triazin-5(4H)-one 145.7g (0.68mol), molar yield 90.66%, detected by HPLC external standard method, 4-amino-6-tert-butyl-3-methylthio- The content of 1,2,4-triazin-5(4H)-one is 96.28%. The detection conditions of the HPLC external standard method are: American waters high-perf...

Embodiment 2

[0030] Acetone 800mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 300g (1.5mol), anhydrous sodium carbonate 397.5g (3.75mol), Add 2 g of potassium iodide into a 2000 mL four-necked reaction flask, slowly add 302.4 g (2.4 mol) of dimethyl sulfate dropwise at a controlled temperature of 30-35 °C under stirring conditions, and after the addition is complete, keep the temperature at 30-35 °C for 4 hours. At the end of the heat preservation reaction, concentrate under negative pressure to evaporate the acetone, recover the acetone, then add 1200mL of water, stir rapidly, separate by suction filtration, and dry under vacuum at 60°C to obtain 4-amino-6-tert-butyl-3-methylthio-1, 2,4-Triazin-5(4H)-one 300g (1.4 mol), the molar yield is 93.45%, detected by HPLC external standard method, 4-amino-6-tert-butyl-3-methylthio-1 , The content of 2,4-triazin-5(4H)-one is 97.31%. The detection conditions of the HPLC external standard method are the same as in Example 1.

Embodiment 3

[0032] Acetone 600mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 200g (1.0mol), anhydrous sodium carbonate 159g (1.5mol), potassium iodide Add 1.5g into a 2000mL four-necked reaction flask, and slowly add 201.6g (1.6mol) of dimethyl sulfate dropwise at a controlled temperature of 40-45°C under stirring conditions. After the addition is complete, keep the temperature at 40-45°C for 5 hours. At the end of the heat preservation reaction, concentrate under negative pressure to evaporate the acetone, recover the acetone, then add 800mL of water, stir rapidly, separate by suction filtration, and dry under vacuum at 60°C to obtain 4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5(4H)-one 200.2g (0.9356 mol), the molar yield is 93.56%, detected by HPLC external standard method, 4-amino-6-tert-butyl-3-methylthio- The content of 1,2,4-triazin-5(4H)-one is 97.11%. The detection conditions of the HPLC external standard method are the same as in Example 1.

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 discloses a method for synthesizing 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one, which comprises the following steps: by using acetone as solvent and potassium iodide as a catalyst, reacting 4-amino-6-tert-butyl-3-thio-1,2,4-triazine-5(4H)-one, dimethyl sulfate and anhydrous sodium carbonate according to a mol ratio of 1:(1-1.6):(1.5-2.5) while keeping the temperature at 20-45 DEG C for 3-6 hours; and finally, recovering the acetone, adding water to perform precipitation, separating, and drying to obtain the 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one. The raw materials used in the method disclosed by the invention are accessible and low in cost; the method disclosed by the invention is mild in reaction, and the reaction parameters are easy to control, thus ensuring the safety of the production process; the potassium iodide is used as the catalyst, so that the reaction can be quickly and completely performed at normal temperature, thus greatly shortening the production cycle and effectively lowering the production cost; the yield of the product is high and is up to 90% or above; and the product with a content of 96% or above can be directly obtained. Thus, the invention conforms to requirements of industrial production, and has better application prospects.

Description

technical field [0001] The invention relates to the technical field of synthesis of triazinone herbicides, in particular to a synthesis of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H )-ketone method. Background technique [0002] 4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one, the trade name is metrimetrione, also known as Saikezin, Rickol, molecular formula :C 8 h 14 N 4 OS, molecular weight: 214.28. It is a systemic selective herbicide, mainly absorbed through roots, stems and leaves, and has good control effect on annual broad-leaved weeds and some gramineous weeds. It is currently one of the most widely used herbicides in the world one. At present, there are many manufacturers of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one, and the synthesis of finished products mainly adopts the following two methods: [0003] One, methyl bromide method, its reaction equation is: [0004] ; [0005] Two, methanol sulfuric acid method, its re...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/075
Inventor 王利明夏秋景陈洁
Owner 苏州诚和医药化学有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com