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2-Mercapto-5-Methyl-1,3,4-Thiadiazole CAS 29490-19-5

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: 2-Mercapto-5-Methyl-1,3,4-Thiadiazole Supplement

Basic Info of 2-Mercapto-5-Methyl-1,3,4-Thiadiazole

What is 2-Mercapto-5-Methyl-1,3,4-Thiadiazole?

Thiadiazole generally refers to 2-mercapto-5-methyl-1,3,4-thiadiazole. 2-Mercapto-5-methyl-1,3,4-thiadiazole is a white crystalline powder, an important intermediate for the synthesis of antibiotic drug cefazolin sodium, and has important industrial and medical value.

The existing preparation method of 2-mercapto-5-methyl-1,3,4-thiadiazole mainly uses hydrazine hydrate, ethyl acetate, methanol or ethanol solvent, lye, carbon disulfide, acid solution as raw materials, wherein, The solvent adopts methanol or ethanol, the alkali solution adopts potassium hydroxide or liquid ammonia, and the acid solution adopts concentrated sulfuric acid or concentrated hydrochloric acid, which is obtained by hydrazation, addition, cyclization and hydrolysis of ethyl acetate.

The existing preparation method of 2-mercapto-5-methyl-1,3,4-thiadiazole has the disadvantages of long reaction time, large energy consumption, complicated and tedious operation, high production cost, and at the same time, it is easy to generate a lot of waste and waste. inadequacy of pollutants.

2-Mercapto-5-Methyl-1,3,4-Thiadiazole Uses

  1. 2-Mercapto-5-methyl-1,3,4-thiadiazole (cefazolin EP impulse E) is a new powerful nitrification inhibitor. It is also an intermediate in the synthesis of thiazolyl Acetylglycine oxime (t344230).
  2. 2-Mercapto-5-methyl-1,3,4-thiadiazole is a pharmaceutical intermediate. The degradation of 2-mercapto-5-methyl-1,3,4-thiadiazole induced by UV and UV / H 2O 2 has been studied.
  3. 2-Mercapto-5-methyl-1,3,4-thiadiazole is an intermediate of the antibiotic cephalosporin V, mainly used as an intermediate of cefazolin sodium (Pioneer No. 5).

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Application of 2-Mercapto-5-Methyl-1,3,4-Thiadiazole

Cefazedone belongs to the first generation of injectable cephalosporin antibiotics. Cefazolin and cefotaxime have significantly better drug resistance than the latter. They are classic broad-spectrum antibiotics with broad antibacterial spectrum and wide clinical application. The results of clinical research trials involving a total of 732 patients in 35 hospitals in 7 countries abroad show that cefoxidone is effective in urinary tract infections, respiratory infections, surgical-skin infections, and gynecological infections caused by Gram-positive and negative bacteria. , biliary tract-abdominal infection, various complex infections, and the effective rate of prevention and treatment in neonates are all above 90%.

CN201510398276.4 provides a kind of synthetic method of novel cephalosporin anti-infective drug cefoxidone sodium with mild production conditions, simple production process, few side reactions, and high product yield and purity.

The present invention adopts the following technical solutions to realize:

A synthesis technique of a novel cephalosporin anti-infective drug is characterized in that comprising the following steps:

  1. Synthesized from 3,5-dichloro-4-pyridone-1-acetic acid (formula I) and 2-mercapto-5-methyl-1,3,4-thiadiazole (formula II) as raw materials Preparation of thioester compound (formula III):

    Dissolve 3,5-dichloro-4-pyridone-1-acetic acid (formula I) and 2-mercapto-5-methyl-1,3,4-thiadiazole (formula II) in an organic solvent, add The organic base was stirred and reacted at room temperature for 1 hour, and then slowly added dropwise the organic solvent solution dissolved with the catalyst, the dropwise addition was completed within 1-2 hours, the temperature was controlled at 20-25°C, and the reaction was stirred for 1-2 hours, filtered, and the filtrate was cooled to 10°C Below, the crystals are precipitated, suction filtered, and dried to obtain the thioester compound (formula III);

  2. Preparation of cefoxidone sodium (formula IV):

    Under the protection of nitrogen, add 7-ACA and sodium bicarbonate into a mixed solvent of water and ethanol, stir to dissolve, add the thioester compound (formula III) obtained in step (1), control the temperature to react, and then Adjust the pH value with sodium bicarbonate; decolorize with activated carbon, crystallize, filter, wash, and dry to obtain the product cefoxidone sodium (formula IV).

Preparation of 2-Mercapto-5-Methyl-1,3,4-Thiadiazole

CN201310293603.0 for the existing preparation method of 2-mercapto-5-methyl-1,3,4-thiadiazole has long reaction time, large energy consumption, complicated and tedious operation, high production cost, and is easy to produce Due to the shortcomings of more wastes and pollutants, a 2-mercapto-5-methyl-1,3,4- 2-mercapto-5-methyl-1,3,4- The preparation method of thiadiazole.

The technical scheme of the present invention is achieved by the following methods: a preparation method of 2-mercapto-5-methyl-1,3,4-thiadiazole, the 2-mercapto-5-methyl-1,3, The preparation method of 4-thiadiazole comprises the following steps:

  • Put the weighed hydrazine hydrate and ammonia water into the reaction vessel and mix evenly, add carbon disulfide dropwise at a temperature lower than 5 °C, and stir and keep warm for 0.5 to 1 h after the dropwise addition to obtain an aqueous solution of ammonium hydrazine dithiocarboxylate , the reaction formula is as follows:
  • Add acetonitrile into the reaction vessel, stir and react for 1 to 2 hours, then raise the temperature of the reaction solution to 85 to 90 °C, stir and maintain reflux for 0.5 to 1 hour to obtain 2-mercapto-5-methyl-1,3,4-thiazide Aqueous solution of oxadiazole ammonium salt, its reaction formula is as follows:
  • When the temperature of the reaction vessel in step (2) is cooled to below 40°C, add hydrochloric acid dropwise to acidify to obtain 2-methyl-5-mercapto-1,3,4-thiadiazole suspension, filter and wash to obtain milky white crystal powder That is, the crude product of 2-mercapto-5-methyl-1,3,4-thiadiazole is purified and dried to obtain 2-mercapto-5-methyl-1,3,4-thiadiazole as a white crystalline powder. The reaction formula is as follows:

Compared with the existing preparation method of 2-mercapto-5-methyl-1,3,4-thiadiazole, the present invention has the following characteristics:

  1. The raw materials used are relatively reduced, the process steps are simplified, and the synthesis process is carried out in one step, which not only shortens the production cycle, reduces the cost of raw materials, but also improves the product yield and product quality.
  2. In the synthesis process, no organic solvent such as methanol and ethanol is used, so that the reaction becomes a reaction using water as a solvent. Compared with the reaction in the organic solvent, the reaction in the water solvent is simple, the reaction operation is simple, the solvent does not need to be separated out, the energy is saved, the loss of the intermediate product is prevented, the product yield is improved, and the It has the advantages of waste generation and environmental pollution caused by toxic and harmful substances.

Renference

  1. 2-Mercapto-5-Methyl-1,3,4-Thiadiazole – ChemicalBook
  2. 2-Mercapto-5-Methyl-1,3,4-Thiadiazole – PubChem
  3. CN201310293603.0 A kind of preparation method of 2-mercapto-5-methyl-1,3,4-thiadiazole
  4. CN201510398276.4 Synthesis process of a novel cephalosporin anti-infective drug

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