Method for synthesizing TTZ (thiotriazinone) by using self-made organic base catalyst taking graphene as carrier

A base catalyst and graphene technology, applied in organic compound/hydride/coordination complex catalysts, organic chemistry, chemical instruments and methods, etc., can solve the problem of high production cost of triazine rings, refractory or processing costs, partial Concentration unevenness and other problems, to achieve the effect of reducing environmental protection investment, reducing the amount of waste, and easy to control

Inactive Publication Date: 2017-05-31
SHANDONG HUIHAI PHARMA & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 1. The material in the reaction system is relatively viscous, the local concentration is uneven, and many by-products are formed, resulting in a low cyclization yield, only 55-65%;
[0008] 2. There are many impurities. The by-product 1-methyl-5-mercapto-1,2,4-triazole-3-carboxylic acid methyl este

Method used

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  • Method for synthesizing TTZ (thiotriazinone) by using self-made organic base catalyst taking graphene as carrier
  • Method for synthesizing TTZ (thiotriazinone) by using self-made organic base catalyst taking graphene as carrier
  • Method for synthesizing TTZ (thiotriazinone) by using self-made organic base catalyst taking graphene as carrier

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Add 180kg of 2-methylthiosemicarbazide, 315kg of diethyl oxalate, 1260kg of methanol solvent, 228kg of self-made alkali catalyst with graphene as the carrier, and carry out ring closure reaction at 0-60°C. After the reaction is completed, decolorize , acidified with hydrochloric acid, filtered and dried to obtain a triazine ring with a yield of 85.8% and a by-product of 85 ppm. The HPLC spectrum of the triazine ring is as follows figure 1 As shown, the small peak 3 minutes before the main peak is the peak of the by-product 1-methyl-5-mercapto-1,2,4-triazole-3-carboxylic acid methyl ester.

Embodiment 2

[0024] Add 180kg of 2-methylthiosemicarbazide, 270kg of diethyl oxalate, 1080kg of methanol solvent, 230kg of self-made alkali catalyst with graphene as the carrier, and carry out ring closure reaction at 0-60°C. After the reaction is completed, decolorize 1. After acidifying with hydrochloric acid, filter and dry to obtain a triazine ring with a yield of 85.2% and a by-product of 90 ppm. The HPLC spectrum of the triazine ring is as follows figure 2 As shown, the small peak 3 minutes before the main peak is the peak of the by-product 1-methyl-5-mercapto-1,2,4-triazole-3-carboxylic acid methyl ester.

Embodiment 3

[0026] Add 180kg of 2-methylthiosemicarbazide, 360kg of diethyl oxalate, 2160kg of methanol solvent, 270kg of self-made alkali catalyst with graphene as the carrier, and carry out ring closure reaction at 0-60°C. After the reaction is completed, decolorize 1. After acidifying with hydrochloric acid, filter and dry to obtain a triazine ring with a yield of 85.6% and a by-product of 95 ppm. The HPLC spectrum of the triazine ring is as follows image 3 As shown, the small peak 3 minutes before the main peak is the peak of the by-product 1-methyl-5-mercapto-1,2,4-triazole-3-carboxylic acid methyl ester.

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Abstract

The invention relates to a method for synthesizing TTZ (thiotriazinone) by using a self-made organic base catalyst taking graphene as a carrier. The method comprises steps as follows: 2-methyl thiosemicarbazide, diethyl oxalate, the self-made base catalyst taking graphene as the carrier and methanol are subjected to a cyclization reaction at 0-60 DEG C to produce sodium TTZ, the graphene carrier is separated through decolorization and filtration, acidification with hydrochloric acid is performed, and TTZ is obtained. The self-made base catalyst taking graphene as the carrier is used, so that the reaction is conducted in a homogeneous reaction system, the reaction yield is increased, the cyclization yield of TTZ is increased to 85% (in terms of 2-methylthiourea) or above, meanwhile, the viscosity of the reaction system is reduced, and the reaction is easy to control; the content of byproduct 1-methyl-5-thiol-1,2,4-triazole-3-methyl carboxylate is controlled at 100 ppm or below, and the product quality is improved; due to increase of the yield, the utilization rate of raw materials is increased, environmental protection investment is reduced, and the production cost is reduced.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing a triazine ring using a self-made organic base catalyst with graphene as a carrier. Background technique [0002] Triazine ring (TTZ) is a key intermediate for the synthesis of ceftriaxone sodium, and after synthesizing 7-ACT with 7-ACA, ceftriaxone sodium can be synthesized with DAMA, so it is an important intermediate for the production of ceftriaxone sodium. It plays a key role in the production of ceftriaxone sodium. Ceftriaxone sodium, also known as ceftriaxone, is a landmark third-generation cephalosporin antibiotic (trade name: Rocephine) developed by Roche, Switzerland. It was first listed in Switzerland in 1982 and is the first semi-synthetic Broad-spectrum long-acting cephalosporins are mainly used for infections caused by sensitive bacteria, such as respiratory infections (especially pneumonia), ear, nose and throat inf...

Claims

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Application Information

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IPC IPC(8): C07D253/075B01J31/26
CPCB01J31/26B01J2231/4283C07D253/075
Inventor 于西波曲良体郑庚修牟应科卢言建王乐强孙成斌
Owner SHANDONG HUIHAI PHARMA & CHEM
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