Synthesis method of thiazole-4-formaldehyde

Abstract

The invention provides a synthesis method of thiazole-4-formaldehyde. The method comprises the following steps: using simple, common and cheap 2-amino-thiazole-4-methyl formate as raw material to perform diazotization and remove 2-amino, reducing with hypophosphrous acid to obtain thiazole-4-methyl formate, and reducing with dibal-H diisobutylaluminum hydride to obtain thiazole-4-formaldehyde. The method solves the defects that the mass production of thiazole-4-formaldehyde can not be realized; and the invention provides the industrial production method of thiazole-4-formaldehyde which is easy to operate and realize. The raw material of the synthesis method has simple preparation method and low price; and the preparation operation is simple and the industrial production is easy to realize.

Description

technical field [0001] The invention relates to a method for synthesizing high-purity chemical product thiazole-4-carbaldehyde. Background technique [0002] As a pharmaceutical intermediate and fine chemical raw material, thiazole-4-carbaldehyde plays a vital role in the production of its follow-up products. In recent years, with the continuous development of its downstream products, the global demand for thiazole-4-carbaldehyde is increasing year by year. However, the technical information on the synthesis of thiazole-4-carbaldehyde comes from relevant foreign literature, and there are almost no reports on its synthetic route in China. According to foreign literature reports, its preparation and production methods are relatively difficult, and the cost of raw materials is relatively high. [0003] Foreign language materials Journal of Medicinal Chemistry, 50(8), 1850-1864; 2007 uses thiazole-4-carboxylic acid as the starting material, reacts with thionyl chloride and Wei...

AI Technical Summary

Problems solved by technology

However, the synthetic technical data about thiazole-4-carboxaldehyde all come from relevant foreign literature, and there are almost no reports on the research on its synthetic route in China.

According to foreign literature reports, its preparation and production methods are relatively difficult, and the cost of raw materials is relatively high

[0003] Foreign language materials Journal of Medicinal Chemistry, 50(8), 1850-1864; 2007 uses thiazole-4-carboxylic acid as the starting material, reacts with thionyl chloride and Weinreb amine to form an amide, and then reduces it with lithium aluminum hydride to obtain thiazole -4-formaldehyde, the starting material thiazole-4-formic acid of this route also needs longer production cycle, and the reaction process will cause greater pollution to the environment

Foreign language materials Heterocycles, 63(10), 2385-2392; 2004 is based on thiazole-4-methyl as the starting material, dichlorination on the 4-methyl group and then reacting with sulfuric acid to obtain thiazole-4-carbaldehyde, Among them, the first step reaction requires about 90°C, and the second step requires about 125°C. The reaction temperature of the two steps is relatively high, consumes a lot of energy, and is not suitable for industrial production.

Foreign language information Helvetica Chimica Acta, 34, 143-8; 1951 is based on the thiosulfone azide compound of thiazole-4-carboxylic acid as the starting material and then reacted with sodium carbonate and glycerin to obtain thiazole-4-carbaldehyde, the reaction yield is only 25%, and the synthesis of starting materials for the reaction is relatively difficult

It can be seen that most of the methods reported in foreign languages ​​have certain disadvantages, either the preparation method of the required raw materials is difficult, or the method itself is not suitable for quantitative production, etc.

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