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A kind of synthetic method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4h)-one

A synthesis method and tert-butyl technology are applied in the synthesis field of triazinone herbicides, which can solve the problems of difficulty in controlling production risk, difficult procurement of raw materials, poor product quality, etc., and achieve good application prospects and easy control of reaction parameters. , The effect of reducing the production cycle

Active Publication Date: 2016-01-20
苏州诚和医药化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Acetone 400mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 150g (0.75mol), anhydrous sodium carbonate 120g (1.13mol), potassium iodide 1g was added to a 1000mL four-necked reaction flask, and 102g (0.81mol) of dimethyl sulfate was slowly added dropwise at a controlled temperature of 25-30°C under stirring conditions. 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-performance liquid chromatography, C18 chromatographic column, size 150mm×4.6mm; mobile ph...

Embodiment 2

[0031] Acetone 800mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 300g (1.5mol), anhydrous sodium carbonate 287g (2.71mol), potassium iodide 2g was added to a 2000mL four-necked reaction flask, and 245.7g (1.95mol) of dimethyl sulfate was slowly added dropwise at a controlled temperature of 30-35°C under stirring conditions. 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 293.6g (1.37mol), the molar yield is 91.33%, detected by HPLC external standard method, 4-amino-6-tert-butyl-3-methylthio- The content of 1,2,4-triazin-5(4H)-one is 96.31%. The detection conditions of the HPLC external standard method are the same as in Example 1.

Embodiment 3

[0033] Acetone 800mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 300g (1.5mol), anhydrous sodium carbonate 315g (2.97mol), potassium iodide 2g was added to a 2000mL four-necked reaction flask, and 280g (2.22mol) of dimethyl sulfate was slowly added dropwise under stirring at a controlled temperature of 35-40°C. After the addition was complete, the temperature was kept at 35-40°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 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 (1.4mol), molar yield 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.

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Abstract

The invention discloses a synthesis method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one, which comprises a molar ratio of 1:1.05 ~1.5:1.5~2 of 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one, dimethyl sulfate and anhydrous sodium carbonate, solvent acetone, Catalyst potassium iodide, heat preservation reaction at 15-45°C for 2-5 hours, finally recover acetone, add water to precipitate, separate and dry to obtain 4-amino-6-tert-butyl-3-methylthio-1,2,4- Triazin-5(4H)-one. The raw materials used in the method of the present invention are easy to get, and the price is low; The method of the present invention has mild reaction, easy control of reaction parameters, and can ensure the safety of the production process; Potassium iodide is used as the catalyst, which makes the rapid reaction complete at normal temperature, greatly reducing the Its production cycle effectively reduces the production cost; the product yield is high, reaching over 90%, and products with a content of over 96% can be directly obtained, which meets the requirements of industrial production and has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of synthesis of triazinone herbicides, specifically, a 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H) - Synthesis of ketones. 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 reaction e...

Claims

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Application Information

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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
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