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Deuterated bensulfuron-methyl and intermediate 2-amino-4,6-dideutero methoxypyridine and preparation method thereof

A technology for substituted methoxypyrimidine and bensulfuron-methyl compound, which is applied in the field of deuterated bensulfuron-methyl and intermediate 2-amino-4,6-dideuterated methoxypyrimidine and preparation, and can solve difficult problems. Control the quality of deuterated compounds, the inability to separate deuterium-substituted compounds and hydrogen-substituted compounds, etc.

Inactive Publication Date: 2011-06-08
天津博纳健康产业发展有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, due to the limited variety of deuterated reagents, it is usually difficult to select suitable deuterated synthetic raw materials, so the synthesis work may require some unconventional methods and reaction routes with harsh reaction conditions; Substituted compounds are almost impossible to separate under the conditions of existing separation techniques. Therefore, it is necessary to ensure that the deuterium is completely substituted in the deuterium synthesis, and only contains a small amount of corresponding hydrogen-substituted impurities. Third, in the quality research method, it is difficult to control deuterium To determine the quality of substituted compounds, many special methods for structure confirmation and content determination are required.

Method used

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  • Deuterated bensulfuron-methyl and intermediate 2-amino-4,6-dideutero methoxypyridine and preparation method thereof
  • Deuterated bensulfuron-methyl and intermediate 2-amino-4,6-dideutero methoxypyridine and preparation method thereof
  • Deuterated bensulfuron-methyl and intermediate 2-amino-4,6-dideutero methoxypyridine and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0070] Example 1: Preparation of deuterated core unit 2-amino-4,6-dideuteriomethoxypyrimidine

[0071] Add 1g of sodium metal into a 50ml three-necked flask equipped with a stirring and condensing tube, then place 10ml of deuterated methanol in a constant pressure dropping funnel, and slowly drop it into the bottle depending on the boiling condition. After the sodium metal is completely reacted, 2 g of refined 2-amino-4,6-dichloropyrimidine is added, heated to 70° C. and refluxed for 6 hours. After the reaction, it was naturally cooled to room temperature, filtered, and then the filtrate was concentrated under reduced pressure, methanol was distilled off, and 6ml of water was added to precipitate a white solid. The resulting product is filtered and washed with water, dried, and weighed to obtain 1.25 g of the product

[0072] Deuterated core unit purity evaluation method:

[0073] The purity of 2-amino-4,6-dideuteriomethoxypyrimidine prepared in this experiment was analyzed ...

Embodiment 2

[0076] Embodiment 2: Preparation of deuterated bensulfuron-methyl

[0077] Add 1.15 g of o-ethoxyformyl benzylsulfonamide, 0.02 g of hexamethylenediamine and 10 ml of re-distilled dry xylene into a 50 ml three-neck flask equipped with a stirring and condensing tube, and then 0.54 g of solid trimerized Gas-dissolved in 6ml of re-evaporated and dried xylene and placed in a constant-pressure dropping funnel. The entire system needs to be shielded from light and air and protected with nitrogen, and a drying device and an exhaust gas absorption system should be installed. Heat the reaction bottle with an oil bath until the temperature of the reaction material is 90°C, start to slowly add the xylene solution of trimeric phosgene dropwise, take about three hours to complete the dropwise addition, and then reflux for another 2 hours.

[0078] Cool down to room temperature naturally after the reaction, filter, then concentrate the filtrate under reduced pressure, distill off most of th...

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Abstract

The invention relates to two new compounds containing isotopes, namely 3-(4,6-dideutero methoxypyridine-2-yl)-1-(2-methoxy carbonylphenyl)sulfonylurea (deuterated bensulfuron-methyl D6 for short), and a deuterated core unit thereof, namely 2-amino-4,6-dideutero methoxypyridine. The deuterated bensulfuron-methyl D6 is prepared by further synthesizing the deuterated core unit serving as a raw material; and the two new compounds are characterized in that: two methoxy groups in a molecule are provided with six deuterium atoms; deuterated compounds have the chemical structure same as a bensulfuron-methyl herbicide, and are commonly used for detecting pesticides, pesticide residue and environment to serve as an internal standard; and the deuterated bensulfuron-methyl and the deuterated core unit thereof are identified and detected by nuclear magnetic resonance spectroscopy, high performance liquid chromatography-mass spectrometry and liquid chromatography.

Description

field of invention [0001] The present invention relates to two new compounds containing isotopes, 3-(4,6-dideuteriomethoxypyrimidin-2-yl)-1-(2-methoxycarbonylphenyl)sulfonylurea (abbreviation: deuterated Bensulfuron-methyl D6) and its deuterated core unit 2-amino-4,6-dideuteriomethoxypyrimidine. Deuterated bensulfuron-methyl D6 is widely used as an internal standard in the detection of pesticides, pesticide residues, and the environment. The deuterated bensulfuron-methyl and its intermediate deuterated core unit and preparation methods are introduced. Background technique [0002] Food is the most important basic substance in human life, and food safety is a major issue related to human health and the national economy and people's livelihood. In recent years, with the sustained and rapid development of agriculture and animal husbandry, the extensive use of chemical fertilizers, pesticides, veterinary drugs, growth regulators and other agrochemicals has brought huge economic...

Claims

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Application Information

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IPC IPC(8): C07D239/52C07B59/00
Inventor 汪群杰陈大舟王铨
Owner 天津博纳健康产业发展有限公司
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