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Metribuzin synthesis method

A synthesis method and technology of mezotrione are applied in the field of efficient mezotrione synthesis, and can solve the problems of high cost of process raw materials, low content, long reaction time and the like

Pending Publication Date: 2020-12-01
LIAONING ZHONGHUI BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, dimethyl sulfate is also a highly toxic substance. At the same time, the yield and content of mecitrione in this process are not high, which leads to high cost of process raw materials
Mentioned in CN103333129 that methanol sulfuric acid method is used to synthesize metrizone, but it is pointed out that the yield of this method is very low, and the reaction time is also very long

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0063] Add 200 grams of 6-tert-butyl-4-amino-3-mercapto-1,2,4-triazin-5(4H)-one to 400 grams of 98% sulfuric acid, heat to completely dissolve and clarify, then cool down to 40°C , add 39 grams of methanol dropwise, after the dropwise addition, heat up to 70-75°C and keep the temperature for 7 hours, then cool down to 20-30°C, add 200g of water dropwise, at this time a large amount of material precipitates out, which is metrizone sulfate. The sulfate was suspended in 300 grams of toluene, then added dropwise with 30% sodium hydroxide solution to neutralize to a pH of about 9, allowed to stand for stratification, and the upper organic phase was cooled to 0°C to crystallize, filtered, and dried to obtain 190 grams Mecitrione, the content is 98.6%.

Embodiment 2

[0065] In 400 grams of 98% sulfuric acid, 39 grams of methanol was added dropwise, and after cooling to 40°C, 200 grams of 6-tert-butyl-4-amino-3-mercapto-1,2,4-triazine-5 ( After adding 4H)-ketone, raise the temperature to 70-75°C and keep it warm for 7 hours, cool down to 20-30°C, add 200 grams of water dropwise, at this time a large amount of material precipitates out, which is metrizone sulfate, and this sulfate Suspended in 300 grams of toluene, then added dropwise 30% sodium hydroxide solution to neutralize to a pH of about 9, allowed to stand for stratification, cooled the upper organic phase to 0°C to crystallize, filtered, and dried to obtain 188 grams of azimidone , content 98.5%.

Embodiment 3

[0067] Add 200 grams of 6-tert-butyl-4-amino-3-mercapto-1,2,4-triazin-5(4H)-one to 400 grams of 98% sulfuric acid, heat to completely dissolve and clarify, then cool down to 40°C , add 39 grams of methanol dropwise, after the dropwise addition, heat up to 70-75°C and keep the temperature for 7 hours, then cool down to 20-30°C, add 200g of water dropwise, at this time a large amount of material precipitates out, which is metrizone sulfate. The sulfate was suspended in 300 grams of xylene, then added dropwise with 30% sodium hydroxide solution to neutralize to a pH of about 9, allowed to stand for stratification, and the upper organic phase was cooled to 0°C to crystallize, filtered, and dried to obtain 185 Chrysintrione, content 98.2%.

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Abstract

The invention provides a novel metribuzin synthesis method which comprises the following steps: (1) adding 6-tert-butyl-4-amino-3-sulfydryl-1, 2, 4-triazine-5 (4H)-ketone into a certain amount of sulfuric acid in batches, and heating until the 6-tert-butyl-4-amino-3-sulfydryl-1, 2, 4-triazine-5 (4H)-ketone is completely dissolved and clarified; 2) cooling to a certain feeding temperature, adding acertain amount of methanol, controlling the temperature to a certain temperature, carrying out a heat preservation reaction for a period of time, and cooling the reaction material to a certain temperature for post-treatment; 3) dropwise adding a certain amount of water into the reaction material, and separating out a large amount of material, namely metribuzin sulfate; and 4) suspending the precipitated metribuzin sulfate in a certain amount of solvent, then adding alkali for neutralization, standing for layering, slowly cooling an organic phase for crystallization, and filtering to obtain high-purity metribuzin. The method is smooth in process, mild in condition and environmentally friendly, metribuzin with the purity of 98% or above can be directly obtained, and the yield can reach 85%or above.

Description

technical field [0001] The present invention relates to the field of organic synthesis. Specifically, the present invention relates to a highly efficient method for synthesizing metrizone. Background technique [0002] Mecitrione (6-tert-butyl-4-amino-3-mercapto-1,2,4-triazin-5(4H)-one) is a selective herbicide with high efficiency and low toxicity developed by German Bayer company , can be used in upland crops such as soybean and corn. At present, there are few reports on the synthesis process of metrizone with high content. Most of the studies on the synthesis process focus on methylating reagents. For example, CN1071181169 reports using methylating reagents such as methyl bromide and methyl iodide to synthesize metrizone. However, such methylating reagents are highly toxic, unsafe and environmentally friendly, and the country has explicitly restricted their use. CN103333129 reports the use of dimethyl sulfate as a methylating agent. However, dimethyl sulfate is also...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/075
CPCC07D253/075
Inventor 郭建法李鹏涛吴军军许波稳
Owner LIAONING ZHONGHUI BIOTECHNOLOGY CO LTD
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