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A kind of preparation method of 4-methyl-5-thiazole formaldehyde

A technology of methyl thiazole and formyl thiazole, applied in the direction of organic chemistry and the like, can solve the problems of intractable treatment, a large amount of waste water, waste salt, low reaction yield, etc., and achieve the effects of mild conditions, improved yield, and high yield

Active Publication Date: 2020-08-04
JINAN ENLIGHTEN BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 4-Methyl-5-thiazole carboxaldehyde is an important side chain in the production of cefditoren axetil. Although there are many studies on this compound, it is rarely used in production
The raw materials used in this method are easy to obtain, but the main problem is that the diazotization deamination step will produce a large amount of waste water and waste salt, which are difficult to handle, and the reaction yield is low, so it is not suitable for industrial production.

Method used

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  • A kind of preparation method of 4-methyl-5-thiazole formaldehyde
  • A kind of preparation method of 4-methyl-5-thiazole formaldehyde
  • A kind of preparation method of 4-methyl-5-thiazole formaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Preparation of 2-aminomethyl-4-methylthiazole (G)

[0042]Add 18kg of 2-amino-4-methylthiazole to a 200L enamel reaction kettle, add 80kg of process water, 9.0kg of caustic soda, turn on stirring and cooling, open the interlayer to freeze and cool down; keep the internal temperature at about -5°C, and start adding 23kg dropwise Dimethyl sulfate, control the rate of addition, keep the internal temperature at around 0°C, and finish the addition within 2 hours. After dropping, keep warm for 3 hours. Raise the temperature to about 25-30°C, and keep it warm for 1 hour. Inject 25kg of ethyl acetate into the kettle to extract for the first time. Stand still for 0.5 hour, separate the layers, and take the lower aqueous phase with 15kg of dichloromethane for the second time. Combine the organic phases and wash the organic phase once with 10 kg of process water. After standing still for 0.5 hour, the layers were separated and the aqueous phase was separated. The organic phas...

Embodiment 2

[0048] This example is the same as Example 1, except that in the preparation of 4-methyl-5-thiazole carboxaldehyde (V), a 10% Pd / C catalyst with a water content of 5% was used, and the yield was 51%.

Embodiment 3

[0050] This example is the same as Example 1, except that in the preparation of 4-methyl-5-thiazole carboxaldehyde (V), a 10% Pd / C catalyst with a water content of 3% was used, and the yield was 27%.

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Abstract

The invention discloses a novel preparation method of 4-methylthiazole-5-carboxaldehyde. The novel preparation method includes the steps of subjecting 2-amino-4-methylthiazole to amino methylation toobtain 2-methylamino-4-methylthiazole, subjecting the 2-methylamino-4-methylthiazole to Vilsmeier reaction to obtain 2-methylamino-4-methyl-5-thiazolecarboxaldehyde, and hydrogenating the 2-methylamino-4-methyl-5-thiazolecarboxaldehyde to remove methylamino to obtain the 4-methylthiazole-5-carboxaldehyde. The preparation method has the advantages of moderate reaction condition, high yield, less generated waste and suitability for mass industrial production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 4-methyl-5-thiazole formaldehyde. Background technique [0002] Fitoren is the third generation of oral cephalosporin antibiotics, which was developed by Japan Meiji Seika Co., Ltd. in 1994. It is used to treat infections caused by Gram-positive and Gram-negative bacteria, especially for grape Gram-positive bacteria of the genus Streptococcus, including Streptococcus pneumoniae, Gram-negative bacteria such as Escherichia coli, Branhamella catarrhalis, Klebsiella, Proteus, and Haemophilus influenzae And anaerobic bacteria such as Peptostreptococcus, Propionibacterium acnes, and Bacteroides have shown strong antibacterial power. my country approved listing in 2001. [0003] 4-Methyl-5-thiazole carboxaldehyde is an important side chain in the production of cefditoren axetil. Although there are many studies on this compound, it is rarely used in production. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/24C07D501/24C07D501/02
CPCC07D277/24C07D501/02C07D501/24
Inventor 高明李新孙斌刘元武李国辉毛浙徽贺军
Owner JINAN ENLIGHTEN BIOTECH CO LTD