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

The technology of tert-butyl group and methylthio group is applied in the field of preparation of triazinone herbicides, which can solve the problems of difficult control of production risk, difficult procurement of raw materials, poor product quality and the like, and achieves good application prospects, low price, The effect of reducing the production cycle

Active Publication Date: 2016-04-06
JIANGSU REPONT PESTICIDE FACTORY
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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 -The preparation 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

[0028] 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: American waters high-performance liquid chromatography, C18 chromatographic column, size 150mm×4.6mm; mobile pha...

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 318g (3mol), potassium iodide 2g Add it into a 2000mL four-necked reaction flask, and slowly add 264.6g (2.1mol) of dimethyl sulfate dropwise at a controlled temperature of 35-40°C under stirring conditions. After the addition is complete, keep the reaction at 35-40°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 (1.4mol), 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.

Embodiment 3

[0032] Acetone 800mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazin-5(4H)-one 300g (1.5mol), anhydrous sodium carbonate 270.3g (2.55mol), Add 2.1g of potassium iodide into a 2000mL four-necked reaction flask, and slowly add 226.8g (1.8mol) of dimethyl sulfate dropwise under stirring at a controlled temperature of 30-35°C. After the addition is complete, keep the reaction temperature at 30-35°C for 2 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 299.4g (1.399mol), the molar yield is 93.27%, detected by HPLC external standard method, 4-amino-6-tert-butyl-3-methylthio- The content of 1,2,4-triazin-5(4H)-one is 97.05%. 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 preparation method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one. The molar ratio is 1:1.1~1.4 : 1.5-2 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 , keep warm at 15-45°C for 2-4 hours, finally recover acetone, add water to precipitate, separate and dry to obtain 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine -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 preparation of triazinone herbicides, in particular to a 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H) - Process for the preparation 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D253/075
Inventor 王利明夏秋景陈洁
Owner JIANGSU REPONT PESTICIDE FACTORY
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