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

Active Publication Date: 2016-04-06
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 method for preparing 4-amino-6-tert-butyl- 3-Methylthio-1,2,4-triazin-5(4H)-one method

Method used

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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 127.2g (1.2mol), Add 1 g of potassium iodide into a 1000 mL four-necked reaction flask, slowly add 113.4 g (0.9 mol) of dimethyl sulfate dropwise at a controlled temperature of 25-30 °C under stirring conditions, and after the addition is complete, keep the temperature at 25-30 °C for 4 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 97.31%. The detection conditions of the HPLC external standard method are: American waters high-performance ...

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 333.9g (3.15mol), Add 2 g of potassium iodide into a 2000 mL four-necked reaction flask, slowly add 283.5 g (2.25 mol) of dimethyl sulfate dropwise at a controlled temperature of 20 to 25 ° C under stirring conditions, and after the addition is complete, keep the temperature at 20 to 25 ° C for 4.5 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 96.28%. 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 169.6g (1.6mol), Add 1.5g of potassium iodide into a 2000mL four-necked reaction flask, and slowly add 189g (1.5mol) of dimethyl sulfate dropwise under stirring at a temperature of 25-30°C. After the addition is complete, keep the temperature at 25-30°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 (0.9356mol), 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.

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Abstract

The invention discloses a method for preparing 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one, which comprises a molar ratio of 1:1.2 ~1.5:1.6~2.1 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 20-30°C for 4-5 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 reaction of the present invention is mild, easy to control the reaction parameters, and can ensure the safety of the production process; Potassium iodide is used as the catalyst, so that the rapid reaction is 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 method for preparing 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 meth...

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 苏州诚和医药化学有限公司
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