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Preparation method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine 5 (4H)-ketone

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, etc., and achieves good application prospects, low price, The effect of reducing the production cycle

Active Publication Date: 2013-10-02
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 into a 2000mL four-neck reaction flask, and 245.7g (1.95mol) of dimethyl sulfate was slowly added dropwise at a temperature of 30 to 35°C under stirring conditions. The heat preservation reaction was completed, the acetone was evaporated by vacuum concentration, acetone was recovered, and then 1200 mL of water was added, stirred rapidly, separated by suction filtration, and dried under vacuum at 60 °C to obtain 4-amino-6-tert-butyl-3-methylthio-1, 2,4-Triazine-5(4H)-one 293.6g (1.37mol), the molar yield was 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 was 96.31%. The detection conditions of HPLC external standard method are: American waters high performance liquid chromatograph, C18 chromatographic column, size 150mm×4.6mm; mobile pha...

Embodiment 2

[0030] Acetone 800mL, 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazine-5(4H)-one 300g (1.5mol), anhydrous sodium carbonate 318g (3mol), potassium iodide 2g It was added into a 2000mL four-neck reaction flask, and 264.6 g (2.1 mol) of dimethyl sulfate was slowly added dropwise at a temperature of 35 to 40°C under stirring conditions. The heat preservation reaction was completed, the acetone was evaporated by vacuum concentration, acetone was recovered, and then 1200 mL of water was added, stirred rapidly, separated by suction filtration, and dried 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 was 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 was 97.31%. The detection conditions of the HPLC external standard method were the same as those 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), 2.1 g of potassium iodide was added to a 2000 mL four-necked reaction flask, and 226.8 g (1.8 mol) of dimethyl sulfate was slowly added dropwise at a temperature of 30 to 35 °C under stirring conditions. The heat preservation reaction was completed, the acetone was evaporated by vacuum concentration, acetone was recovered, and then 1200 mL of water was added, stirred rapidly, separated by suction filtration, and dried under vacuum at 60 °C to obtain 4-amino-6-tert-butyl-3-methylthio-1, 2,4-Triazin-5(4H)-one 299.4g (1.399 mol), the molar yield was 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 was 97.05%. The detection conditions of the HPLC external standard method were the same as those 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-triazine 5 (4H)-ketone. The method comprises steps of: reacting 4-amino-6-tert-butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone, dimethyl sulfate and anhydrous sodium carbonate in a molar ratio of 1:1.1-1.4:1.5-2 in a solvent acetone and in the presence of a catalyst potassium iodide at 15-45 DEG C for 2-4 h; and finally recovering acetone, adding water to dilute the material, separating and drying to obtain the 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine 5 (4H)-ketone. The raw materials used in the method are easily available, and cheap; and the method provided by the invention has advantages of moderate reaction and easily controlled reaction parameters, and can guarantee the safety of the production process. Potassium iodide is used as a catalyst, so as to realize rapid complete reaction at room temperature, reduce the production cycle and effectively reduce production cost; the product yield reaches more than 90%, and products with content of more than 96% can be directly obtained. The preparation method satisfies 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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IPC IPC(8): C07D253/075
Inventor 王利明夏秋景陈洁
Owner JIANGSU REPONT PESTICIDE FACTORY
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