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A kind of synthetic method of isotope-labeled metilcarb-d3

A technology of isotope labeling and synthesis method, which is applied in the field of preparation of organic compounds, can solve problems such as difficult introduction of deuterated isotope labels, and achieve high selectivity, simple process and high yield

Active Publication Date: 2017-03-15
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods have their own advantages, but using the above method to synthesize isotope-labeled amecarb-D 3 Both have deficiencies, and it is difficult to introduce deuterated isotope labels

Method used

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  • A kind of synthetic method of isotope-labeled metilcarb-d3

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preparation example Construction

[0017] Isotope-labeled Methiocarb-D 3 The synthetic method of monomethylamine hydrochloride-D 3 The aqueous solution of the dithiocarboxylate solution is added dropwise to the dimethyl dithiocarboxylate solution, and the intermediate S-methyl-N-methylcarboxylate is obtained after the reaction, and the above-mentioned intermediate is slowly passed into Cl 2 , adding acid-binding agent and m-cresol successively to prepare the marker Medicarb-D 3 , take the following steps:

[0018] (1) in N 2 Under protection, monomethylamine hydrochloride-D 3 Dissolve in water, add dropwise into the dimethyl dithiocarboxylate solution within 5-10 minutes, use alkali to keep the pH of the reaction solution = 8-9, the reaction is mild and exothermic, keep the reaction temperature at 30-60°C, and react for 4-8 hours , until the raw material disappears, and after extraction with dichloromethane, the organic phases are combined, and anhydrous Na 2 SO 4 Dry overnight and concentrate to give int...

Embodiment 1

[0028] in N 2 Under protection, 15mmol monomethylamine hydrochloride-D 3 Dissolve in a small amount of water, add dropwise to 50 mmol dimethyl dithiocarboxylate solution within 5-10 min, and keep the pH of the reaction solution at 8-9 with NaOH. The reaction was mildly exothermic, and the reaction was maintained at 30°C for 8 hours until the raw materials disappeared and the reaction ended. Extract with dichloromethane, combine the organic phases, anhydrous Na 2 SO 4Dry overnight and concentrate to give intermediate S-methyl-N-methylcarboxylate-D as a colorless oil 3 .

[0029] The intermediate S-methyl-N-methylcarboxylate-D 3 Dissolve in dimethyl dithiocarboxylate, cool to -30°C, slowly pass in Cl while stirring 2 , the mixture turned pale yellow during the process, and gradually faded until the color of the reaction solution was colorless, and the reaction was stirred for 1 h.

[0030] in N 2 Under protection, triethylamine was added to the reaction solution to keep ...

Embodiment 2

[0032] in N 2 Under protection, 15mmol monomethylamine hydrochloride-D 3 Dissolve with a small amount of water, add dropwise to 15 mmol dimethyl dithiocarboxylate solution within 5 to 10 min, and use Na 2 CO 3 Keep the pH of the reaction solution = 8-9. The reaction was mildly exothermic, and the reaction was maintained at 60°C for 6 hours until the raw materials disappeared, and the reaction ended. Extract with dichloromethane, combine the organic phases, anhydrous Na 2 SO 4 Dry overnight and concentrate to give intermediate S-methyl-N-methylcarboxylate-D as a colorless oil 3 .

[0033] The intermediate S-methyl-N-methylcarboxylate-D 3 Dissolve in dimethyl dithiocarboxylate, cool to -20°C, slowly pass in Cl while stirring 2 , the mixture turned pale yellow during the process, gradually faded until the color of the reaction solution was colorless, and stirred for 4h.

[0034] in N 2 Under protection, DIEA was added to the reaction solution to keep the pH of the react...

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Abstract

The present invention relates to a synthetic method for isotopically labeled tsumacide-D3. The synthetic method comprises the following steps: dropwise adding an aqueous solution of monomethylamine hydrochloride-D3 into a solution of dithio carboxylic acid dimethylster, carrying out reaction to obtain an intermediate of S-methyl-N-methyl carboxylic acid dimethylster, slowly injecting Cl2 into the intermediate at a low temperature, successively adding an acid-binding agent and metacresol, and preparing the isotopically labeled tsumacide-D3. Compared with the prior art, the deuterium isotopic labeling process in the invention has a simple process and high yield, isotopic abundance is undiluted, and the method is suitable for laboratory production of tsumacide-D3.

Description

technical field [0001] The invention relates to a preparation method of a stable isotope-labeled organic compound, in particular to an isotope-labeled amethocarb-D 3 synthetic method. Background technique [0002] Methiocarb is a moderately toxic insecticide. No carcinogenic, teratogenic, mutagenic effects, but toxic to fish, highly toxic to bees. Due to the widespread use of Methiocarb, food, fruit, water and soil have been polluted. In order to inspect Methiocarb in agricultural products, inspection and quarantine departments often use isotope-labeled Methiocarb-D 3 As an internal standard, it was accurately quantitatively analyzed by isotope dilution mass spectrometry (IDMS), and Methiocarb-D was synthesized 3 It is of great significance to the establishment of my country's food safety system. [0003] The synthesis of deuterium-labeled amethicarb does not have relevant documents at present, and the non-isotope-labeled amethicarb mainly has the following methods: (1)...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/44C07C269/00
Inventor 徐建飞杜晓宁雷雯
Owner SHANGHAI RES INST OF CHEM IND
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