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Preparation method of triazine ring

A technology of triazine ring and ring closure reaction, which is applied in the field of medicine, can solve the problems of unavailable input, prominent environmental protection problems, complex solvents, etc., and achieve the effects of increased product purity, reduced environmental protection costs, and simple treatment of three wastes

Active Publication Date: 2021-04-23
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this patent improves the yield, the solvent is complex, causing many troubles to the later treatment of the three wastes, and the environmental protection problem is difficult to solve
[0014] At present, there are many processes for producing triazine rings in China. The high-yield process has prominent environmental protection problems and cannot be put into the current large-scale industrial production. The low-environmental protection cost process also shows the problem of low yield and cannot achieve high yield. and the two-way advantage of low cost

Method used

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  • Preparation method of triazine ring
  • Preparation method of triazine ring
  • Preparation method of triazine ring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Add 24.2g of 2-methylthiosemicarbazide, 70.5g of diethyl oxalate, and 20g of DMAP into a 500mL three-necked flask with an exhaust gas absorption device, raise the temperature to 50°C, reflux for 1 hour, start to slowly add 12g of sodium metal, continue The reaction was refluxed for 3 hours.

[0052] (2) After the cyclization reaction is completed, add 35% hydrochloric acid to remove excess DMAP and sodium ethoxide, control the pH value to 6.7, cool down and filter to obtain 67.5 g of a wet product of triazine ring sodium salt.

[0053] (3) Add 67.5g of triazine ring sodium salt wet product and 135g of purified water to a 250mL three-necked flask and heat up to 65°C, add 35% hydrochloric acid to adjust the pH value to 1.5, add seed crystals and cool to 10°C for crystallization for 1h, filter , and dried to obtain 32.9 g of the triazine ring product, with a yield of 90.1%, a liquid phase purity of 99.8%, and a mass content of 99.0%.

[0054] After testing, the triazi...

Embodiment 2

[0059] (1) Add 24.2g of 2-methylthiosemicarbazide, 84g of diethyl oxalate and 18g of DMAP into a 500mL three-necked flask equipped with an exhaust gas absorption device, raise the temperature to 60°C, reflux for 1 hour, start slowly adding 13g of sodium metal, and continue to reflux React for 2 hours.

[0060](2) After the cyclization reaction, add 33% hydrochloric acid to remove excess DMAP and sodium ethoxide, control the pH value to 7.5, cool down and filter to obtain 63.6 g of a wet product of triazine ring sodium salt.

[0061] (3) Add 63.6g of triazine ring sodium salt wet product and 127.2g of purified water into a 250mL three-necked flask and raise the temperature to 75°C, add 33% hydrochloric acid to adjust the pH value to 2.5, add seed crystals and cool to 15°C for crystallization for 2 hours, Filtration and drying yielded 32.5 g of the triazine ring product, with a yield of 89.0%, a liquid phase purity of 99.8%, and a mass content of 99.2%.

Embodiment 3

[0063] (1) Add 24.2g of 2-methylthiosemicarbazide, 84g of diethyl oxalate, and 18g of DMAP into a 500mL three-neck flask equipped with an exhaust gas absorption device, raise the temperature to 55°C, reflux for 1 hour, start to slowly add 13g of sodium metal, and continue to reflux React for 2.5 hours.

[0064] (2) After the cyclization reaction is completed, add 36% hydrochloric acid to remove excess DMAP and sodium ethoxide, control the pH value to 7.0, cool down and filter to obtain 65.4 g of a wet product of triazine ring sodium salt.

[0065] (3) Add 65.4g of triazine ring sodium salt wet product and 130.8g of purified water to a 250mL three-necked flask and raise the temperature to 70°C, add 36% hydrochloric acid to adjust the pH value to 2.0, add seed crystals and cool to 12°C for crystallization for 1.5h , filtered, and dried to obtain 33.0 g of the triazine ring product, with a yield of 90.4%, a liquid phase purity of 99.7%, and a mass content of 99.1%.

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a triazine ring. The method comprises the following steps: performing cyclization reaction on 2-methylthiosemicarbazide, diethyl oxalate, dimethylaminopyridine and metal sodium, adding hydrochloric acid for crystal transformation reaction after the cyclization reaction is finished to obtain a triazine ring sodium salt crude product, and adding hydrochloric acid into the triazine ring sodium salt crude product for refining reaction to obtain the triazine ring. The method has the advantages of simple raw materials, high yield, easy treatment and low cost.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of a triazine ring. Background technique [0002] Triazine ring (TTZ) [0003] English name: Thiotriazinone [0004] Molecular weight: 159.16 [0005] ECNO: 58909-39-0 [0006] Physical and chemical properties: melting point ≥ 245°C [0007] Alias: 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-3-mercapto-1,2,4-triazine; triazine acid [0008] Molecular formula: C 4 h 5 N 3 o 2 S [0009] Structural formula: [0010] Uses: Used as intermediates of ceftriaxone sodium, ceftriaxone sodium and other drugs. [0011] Chinese patent CN101701012A discloses a synthesis method of a triazine ring, reacting an aqueous solution of methylhydrazine with ammonium thiocyanate, and then using methanol to obtain a methanol solution of aminomethylthiourea; mixing the methanol solution of aminomethylthiourea with dimethyl oxalate Esters and sodium methoxide cycli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/07
CPCC07D253/07
Inventor 侯乐伟司维森郭磊
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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