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Preparation method of 2-methyl-5-sulfydryl-1, 3, 4-thiadiazole dimer

A technology of thiadiazole dimer and thiadiazole, which is applied in organic chemistry and other fields, can solve the problems that structural analysis and pharmacological research cannot be carried out, and achieve the effect of novel synthetic route, easy-to-obtain product and less side reactions

Pending Publication Date: 2022-05-13
河北合佳创新医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the disadvantage that there is currently no synthesis and preparation method for 2-methyl-5-mercapto-1,3,4-thiadiazole dimer, resulting in the inability to conduct structural analysis and pharmacological research, the present invention provides a simple, Preparation method of easily available and high-purity 2-methyl-5-mercapto-1,3,4-thiadiazole dimer

Method used

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  • Preparation method of 2-methyl-5-sulfydryl-1, 3, 4-thiadiazole dimer
  • Preparation method of 2-methyl-5-sulfydryl-1, 3, 4-thiadiazole dimer

Examples

Experimental program
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Embodiment 1

[0030] Add 420g N,N-dimethylformamide into a 1000ml clean four-necked bottle, start stirring, add 100.0g methylmercaptothiadiazole when the temperature is lowered to 15°C, stir to dissolve, then add 310ml 30% hydrogen peroxide solution dropwise, The process control temperature does not exceed 35°C. After observing crystal precipitation, stop adding the hydrogen peroxide solution dropwise, control the temperature at 30-35°C and stir the crystal for 30 minutes, then continue to add the remaining hydrogen peroxide solution dropwise. After the dropwise addition, control the temperature Stir and react at 30-35°C for 30 minutes, then lower the temperature to 5°C, grow crystals for 30 minutes, and then filter. The filter cake is dried under reduced pressure in an oven at 60°C for 3 hours, and 59.5 g of the target product is obtained after reaching a constant weight. After testing, this example The purity (HPLC) of the target product methylmercaptothiadiazole dimer is 97.9%. The targe...

Embodiment 2

[0041] Add 150g N,N-dimethylacetamide into a 500ml clean four-necked bottle and start stirring. When the temperature is lowered to 13°C, add 26.5g methylmercaptothiadiazole. Oxyacetic acid solution, the process control temperature does not exceed 35°C. After observing that crystals are precipitated, stop dripping the peroxyacetic acid solution, control the temperature at 30-35°C and stir the crystal for 35 minutes, and then continue to drop the remaining peracetic acid solution until the addition is complete. Finally, control the temperature at 30-35°C, stir and react for 30 minutes, then cool down to 9°C, grow crystals for 30 minutes, and then filter. The filter cake is dried in an oven at 50°C under reduced pressure for 3 hours, and 16.9 g of the target product is obtained after reaching a constant weight. , the purity (HPLC) of the target product methylmercaptothiadiazole dimer in this example is 98.4%.

Embodiment 3

[0043] Add 180g dimethyl sulfoxide into a 500ml clean four-necked bottle and start stirring. When the temperature is lowered to 10°C, add 22.0g methylmercaptothiadiazole. After stirring to dissolve, add dropwise 50ml of 30% hydrogen peroxide solution , the process control temperature does not exceed 35°C. After observing that crystals are precipitated, stop adding hydrogen peroxide solution, control the temperature at 30-35°C and stir and grow crystals for 30 minutes, and then continue to add the remaining hydrogen peroxide solution dropwise. After the dropwise addition, control Stir and react at 30-35°C for 30 minutes, then lower the temperature to 7°C, grow crystals for 30 minutes, and then filter. The filter cake is dried in an oven at 70°C for 3 hours under reduced pressure, and 12.4 g of the target product is obtained after reaching a constant weight. After testing, this implementation The purity (HPLC) of the target product methylmercaptothiadiazole dimer is 98.5%.

[00...

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Abstract

The invention discloses a preparation method of a 2-methyl-5-sulfydryl-1, 3, 4-thiadiazole dimer, which is characterized in that when an organic solvent is cooled to 10-15 DEG C, 2-methyl-5-sulfydryl-1, 3, 4-thiadiazole is added for dissolving and clarifying, then a hydrogen peroxide or peracetic acid solution is dropwise added until crystals appear, the temperature is controlled, stirring is performed for growing the crystals, and the 2-methyl-5-sulfydryl-1, 3, 4-thiadiazole dimer is obtained. And continuously dropwise adding a hydrogen peroxide solution or a peracetic acid solution, growing crystals, filtering, and drying to constant weight. The method has the advantages that the route is simple, the product is easy to obtain, the conversion rate of the generated methyl mercaptothiadiazole dimer impurity can reach more than 97.5%, the subsequent treatment steps are simple, the target product is directly separated out, complicated purification steps are not needed, the purity of the target product is high, the highest purity is 98.5%, the single maximum impurity is the residual raw material methyl mercaptothiadiazole, and the method is suitable for industrial production. The content of other impurities is less than 0.2%, and effective structure confirmation can be carried out. According to the invention, the blank of the cefazolin impurity in the research of the cefazolin impurity is filled, and the subsequent structural analysis and pharmacological research of the impurity are facilitated.

Description

technical field [0001] The invention belongs to the field of chemical drug synthesis, in particular to the preparation of 2-methyl-5-mercapto-1,3,4-thiadiazole dimer (methylmercaptothiadiazole dimer) in the quality research of cefazolin sodium Preparation. Background technique [0002] Cefazolin sodium (English common name is Cefazolin Sodium), first developed by Fujisawa Pharmaceutical Co., Ltd. in Japan, was first listed in Japan in 1971. It is the first generation cephalosporin with a wide antibacterial spectrum. It is an international and domestic clinical medical treatment revolution. It is the leading antibiotic for Lambert-positive bacteria. It is clinically used in respiratory tract, genitourinary system, skin and soft tissue, bone and joint, and biliary tract infections caused by sensitive bacteria. It can also be used for endocarditis, sepsis, pharynx and ear infections. It can also be used as prophylaxis before surgery. [0003] In the synthetic routes of cefazo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/12
CPCC07D285/125
Inventor 祁振海程广业周玲玲谷宏伟孙收杰陈芳芳赵瑞欣
Owner 河北合佳创新医药科技有限公司
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