Synthesis method of stable isotope deuterium labeled 2-methyl-4-isothiazole-3-one

A technology of stable isotopes and synthetic methods, applied in the field of isotope deuterium-labeled compound synthesis

Pending Publication Date: 2019-07-23
河南凯美思睿化工科技有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention provides a method for synthesizing 2-methyl-4-isothiazol-3-one labeled with stable isotope deuterium, so as to solve the problem of the synthesis of deuterium-labeled 2-methyl-4-isothiazol-3-one that has not been published in the literature route problem

Method used

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  • Synthesis method of stable isotope deuterium labeled 2-methyl-4-isothiazole-3-one
  • Synthesis method of stable isotope deuterium labeled 2-methyl-4-isothiazole-3-one
  • Synthesis method of stable isotope deuterium labeled 2-methyl-4-isothiazole-3-one

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Embodiment 1

[0025] A synthetic method for labeling 2-methyl-4-isothiazol-3-one with stable isotope deuterium, comprising the following steps:

[0026] Step 1: Select a 100mL schlenk tube and place it on a flame blower, dry the reaction tube under vacuum conditions, and cool the reaction tube under a nitrogen atmosphere. Then add a stirring bar and 3,3'-dimercaptodipropionic acid (6.3 g, 30 mmol) under a nitrogen atmosphere, draw thionyl chloride (4.4 mL, 60 mmol) into the reaction solution quickly with a 5 ml syringe, In addition, 6 drops (about 0.3 mL) of N,N-dimethylformamide were added dropwise to the reaction solution as a catalyst to speed up the reaction. The reaction tube was placed in an oil bath, the oil bath was stably controlled at 30° C., and vigorously stirred for 12 hours, the reaction solution slowly changed from colorless to yellow. The reaction system was lowered to room temperature, and the volatile matter in the solution was removed in a vacuum environment with an oil ...

Embodiment 2

[0036]A synthetic method for stable isotope deuterium-labeled 2-methyl-4-isothiazol-3-one, step 1 and step 2 are the same as in Example 1, the difference is: step 3: deuterated amide (242mg, 1mmol) Place in a 25mL round-bottomed flask, and add 3mL of dichloromethane solvent into the reaction flask. The round bottom flask was placed in an ice-water bath, and sulfuryl chloride (270mg, 2mmol) was slowly added dropwise into the flask. At this time, the solids in the system dissolved slowly and a relatively uniform suspension appeared. The reaction system was continuously stirred in an ice-water bath for about 1 hour, and then continued to stir at room temperature for about 15 hours. At this time, the reaction system became a white suspension. Add potassium carbonate to the reaction system until there were no bubbles, and continue to stir for 10 minutes. Silica gel (2g, 200-300m) was added to the reaction system, and the volatile matter in the system was removed with a rotary evapo...

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Abstract

The invention provides a synthesis method of stable isotope deuterium labeled 2-methyl-4-isothiazol-3-one, the synthesis method comprises the following steps: step 1, taking 3,3'-dimercaptodipropionicacid and thionyl chloride as raw materials, and obtaining 3,3'-dimercaptodipropionyl chloride through catalytic reaction by a catalyst; step 2, after an alkali and a carbonate are sequentially addedto deuterated methylamine hydrochloride, adding the 3,3'-dimercaptodipropionyl chloride obtained in the step 1 to react to obtain deuterated amide; step 3, adding a reaction solvent and sulfonyl chloride to the deuterated amide obtained in the step 2, continuously stirring the reaction system at 0 DEG C for reaction for 1 hour, and then continuously stirring and reacting at room temperature for 15hours to obtain the stable isotope deuterium labeled 2-methyl-4-isothiazol-3-one, wherein the molar ratio of deuterated amide to sulfonyl chloride is 1: 3. According to the invention, the reaction yield can reach 34%, the purity of the target product can reach 98%, and the deuterium generation rate can reach more than 99%.

Description

technical field [0001] The invention relates to the technical field of isotope deuterium-labeled compound synthesis, in particular to a synthesis method of stable isotope deuterium-labeled 2-methyl-4-isothiazol-3-one. Background technique [0002] 2-Methyl-4-isothiazolin-3-one (MIT) is a high-efficiency, broad-spectrum, and good compatibility fungicide, which is widely used in pulp and paper, cosmetics, personal care products, coatings, adhesives, Anticorrosion and sterilization of industrial products such as printing ink and leather. MIT is usually used in combination with 5-chloro-2-methyl-4-isothiazolin-3-one (CMI) at a mass ratio of 1:3, and its trade name is Kathon or Kathon (CG). The fungicide MIT is a kind of sensitizer, it will cause allergy or dermatitis and other symptoms in contact with the skin, and it has certain cytotoxicity and neurotoxicity. There are strict restrictions on the use of related isothiazolinone fungicides in food contact materials, toys, cosme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/03
CPCC07D275/03C07B2200/05
Inventor 闫晓宇曹瑞王佟
Owner 河南凯美思睿化工科技有限公司
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