Method for synthesizing thiotriazinone

A synthesis method and technology of triazine ring, applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of long overall reaction time, waste of time and raw materials, low reaction yield and the like, so as to shorten the reaction time, reduce the cost of raw materials, and reduce the operation effect of steps

Active Publication Date: 2012-07-11
YIYUAN XINQUAN CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, there are problems such as low reaction yield and long overall reaction time, which cause waste of time and raw materials, and have great constraints on actual production.

Method used

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  • Method for synthesizing thiotriazinone
  • Method for synthesizing thiotriazinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Add the mixture of 10.5g of the reaction material 2-methylthiosemicarbazide, 230ml of ethanol, 10.7g of ammonium chloride and 32.1ml of 10wt% hydrochloric acid solution into a three-necked flask, and add diethyl oxalate dropwise when the temperature is controlled at 40°C 14.7 g of ester was added dropwise in 30 minutes, then heated to reflux for 3 hours, cooled to 10°C, filtered and dried to obtain a crude triazine ring.

[0019] (2) Add an appropriate amount of distilled water and the crude product of triazine ring in the reaction flask, heat up, add a small amount of activated carbon after the material is completely dissolved, continue to stir for 30min, heat filtration, cooling, crystallization, filtration, obtain product 12.5g, yield 78.6%.

Embodiment 2

[0021] (1) Add the mixture of 2-methylthiosemicarbazide 10.5g, ethanol 240ml, 11.2g ammonium chloride and 33.6ml 10wt% hydrochloric acid solution into the three-necked flask, and add diethyl oxalate dropwise when the temperature is controlled at 40°C 16.2 g of ester was added dropwise in 30 minutes, then heated to reflux for 3 hours, cooled to 10°C, filtered and dried to obtain a crude triazine ring.

[0022] (2) Add an appropriate amount of distilled water and the crude product of triazine ring in the reaction flask, heat up, add a small amount of activated carbon after the material is completely dissolved, continue to stir for 30min, heat filtration, cooling, crystallization, filtration, obtain product 13.1g, yield 82.4%.

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Abstract

The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing thiotriazinone. The method comprises the following steps of: reacting 2-methylaminothiourea and diethyl oxalate which are taken as raw materials and ethanol which is taken as a solvent to obtain crude thiotriazinone, and recrystallizing the crude thiotriazinone to obtain a final product, wherein a recrystallization solvent is water. The method is characterized in that: a catalyst is added in the reaction of the 2-methylaminothiourea and the diethyl oxalate, and is a mixture of ammonium chloride and a hydrochloric acid solution at the concentration of 10 weight percent. The method has the advantages that: the reaction yield is improved and the reaction time is shortened by selecting the appropriate catalyst; the cost of raw materials is reduced; operation steps are reduced; and the method is more suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing a triazine ring. Background technique [0002] Triazine ring, chemical name: 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-3-mercapto-1,2,4-triazine, molecular formula: C 4 h 5 N 3 o 2 S, the structural formula is as follows: [0003] [0004] Appearance: White or off-white crystalline powder, melting point ≥ 245°C. [0005] Triazine ring is an important pharmaceutical intermediate, mainly used in the synthesis of ceftriaxone sodium. [0006] The triazine ring reacts with 2-methylthiosemicarbazide and diethyl oxalate as raw materials to generate the target compound. The reaction formula is as follows: [0007] [0008] However, there are problems such as low reaction yield and long overall reaction time, resulting in waste of time and raw materials, which greatly restricts actual production. Contents of the invention [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/075
Inventor 蔡杰
Owner YIYUAN XINQUAN CHEM
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