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Synthesis method of stable isotope deuterium labeled methyl triclosan

A stable isotope, methyl triclosan technology, applied in organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of human injury, long process route, high energy consumption, etc. Low harm, easy separation and purification, good economic benefits

Active Publication Date: 2021-06-04
上海安谱璀世标准技术服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the stable isotope deuterium-labeled methyl triclosan products currently on the market are mainly from abroad, and there is no domestic company to independently develop and produce, and the synthesis method of stable isotope deuterium-labeled methyl triclosan has not been reported, only a small amount of literature The data report the synthetic method of methyltriclosan
[0004]Journal of Electroanalytical Chemistry, 2014, 731, 1-5. Using triclosan and dimethyl sulfate to synthesize methyl triclosan under alkaline condition of potassium carbonate Chlorosan, according to this method, triclosan and stable isotope deuterium-labeled dimethyl sulfate can be used to synthesize stable isotope deuterium-labeled methyl triclosan, but dimethyl sulfate is more toxic and will pollute the environment and cause harm to the human body , and stable isotope deuterium-labeled dimethyl sulfate is expensive and costly
[0005] Journal of Electroanalytical Chemistry, 2010, 638(1), 100-108. and Organic Mass Spectrometry, 1985, 20(2), 122-133. and the United States The patent document U.S.6133483 respectively reports the synthesis method of methyl triclosan, but the introduction of the stable isotope deuterium of these three schemes is relatively difficult, the process route will be longer, and high temperature reaction conditions are required, and the energy consumption is relatively large

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  • Synthesis method of stable isotope deuterium labeled methyl triclosan
  • Synthesis method of stable isotope deuterium labeled methyl triclosan
  • Synthesis method of stable isotope deuterium labeled methyl triclosan

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Embodiment 1

[0024] The synthesis process of stable isotope deuterium-labeled methyltriclosan is as follows:

[0025] Dissolve triclosan (7mmol, 2g), deuterated methanol (7.7mmol, 277mg) and triphenylphosphine (7mmol, 1.84g) in anhydrous tetrahydrofuran at 0-5°C, and add 1-2 drops Add a solution of diisopropyl azodicarboxylate (7mmol, 1.42g) in anhydrous tetrahydrofuran dropwise at a rate of 1 / sec. After the dropwise addition, keep the temperature at 0-5°C, stir and react for 1.5 hours, and spin dry the solvent under reduced pressure , separated and purified by column chromatography, the stable isotope deuterium-labeled methyltriclosan-D was obtained with a yield of 85%. 3 , the chemical purity and stable isotope abundance of the obtained product both reach above 99%.

[0026] The product that this embodiment obtains is CDCl 3 As a solvent, it is detected by a Bruke-400 M nuclear magnetic resonance instrument to obtain a hydrogen nuclear magnetic resonance spectrum as shown in figure 1 ...

Embodiment 2

[0029] The synthesis process of stable isotope deuterium-labeled methyltriclosan is as follows:

[0030] Under the condition of 0~5℃, triclosan (3.5mmol, 1g), deuterated methanol (3.8mmol, 137mg) and triphenylphosphine (3.5mmol, 920mg) were dissolved in anhydrous tetrahydrofuran, with 1~2 Add a solution of diethyl azodicarboxylate (3.5mmol, 710mg) dropwise in anhydrous tetrahydrofuran at a rate of drop / second. After the dropwise addition, keep the temperature at 0-5°C, stir for 1 hour, and spin dry the solvent under reduced pressure. , separated and purified by column chromatography, and obtained stable isotope deuterium-labeled methyltriclosan-D with a yield of 80%. 3 .

Embodiment 3

[0032] The synthesis process of stable isotope deuterium-labeled methyltriclosan is as follows:

[0033] Dissolve triclosan (5.2mmol, 1.5g), deuterated methanol (5.7mmol, 206mg) and triphenylphosphine (5.3mmol, 1.38g) in anhydrous dichloromethane at 0-5°C, Add a solution of diisopropyl azodicarboxylate (5.3mmol, 1.07g) in anhydrous dichloromethane dropwise at a rate of 1-2 drops / second. After the addition is completed, keep the temperature at 0-5°C and stir for 2 hour, after the solvent was spin-dried under reduced pressure, column chromatography separation and purification obtained stable isotope deuterium-labeled methyltriclosan-D with a yield of 82%. 3 .

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Abstract

The invention discloses a synthesis method of stable isotope deuterium labeled methyl triclosan. According to the synthesis method, the stable isotope deuterium-labeled methyl triclosan is obtained through one-step reaction of deuterated methanol serving as a source of stable isotope deuterium and triclosan under the effect of a redox coupling reagent by utilizing a Mitsunobu reaction. The synthesis method has the advantages of cheap and easily available stable isotope raw materials, low toxicity, short reaction time, low energy consumption, simple operation, no shedding of stable isotope deuterium, easy separation and purification of the product, high yield, and chemical purity and stable isotope abundance of more than 99%, meets the requirements of a standard reagent for quantitative detection of methyl triclosan, and has high economical efficiency.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, in particular to a method for synthesizing methyl triclosan labeled with stable isotope deuterium. Background technique [0002] Methyltriclosan (2,4,4'-trichloro-2'-methoxydiphenyl ether, MTCS) is triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether , TCS) methylation products, both of which are broad-spectrum fungicides. Due to excessive abuse, they are widely present in water bodies and even organisms, causing pollution, while methyl triclosan has higher lipophilicity, making it Can be more easily and more persistently accumulated in organisms. [0003] Stable isotope dilution mass spectrometry (Isotope Dilution Mass Spectrometry, IDMS) can accurately and quantitatively analyze triclosan and methyltriclosan by using isotope internal standard. However, the stable isotope deuterium-labeled methyl triclosan products currently on the market are mainly from abroad, and there is no...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/18C07C43/29
CPCC07C41/18C07B2200/05C07C43/29Y02P20/55
Inventor 郭会徐敏陈武炼
Owner 上海安谱璀世标准技术服务有限公司