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Novel preparation method for 4-methylthiazole-5-carboxaldehyde

A technology of methyl thiazole and formyl thiazole, applied in the direction of organic chemistry, etc., can solve the problems of difficult treatment, large amount of waste water, waste salt, less application, etc., and achieve the effects of improving yield, mild conditions, and less three wastes

Active Publication Date: 2018-12-21
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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  • Novel preparation method for 4-methylthiazole-5-carboxaldehyde
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  • Novel preparation method for 4-methylthiazole-5-carboxaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0042]In the 200L enamel reaction kettle, add 18kg 2-amino-4-methylthiazole, add 80kg process water, 9.0kg caustic soda, turn on stirring cooling, turn on interlayer freezing and cooling; keep the inner temperature at about -5 ℃, start to drip 23kg Dimethyl sulfate, control the dripping speed, keep the internal temperature at about 0 °C, and finish dripping within 2 hours. After dripping, the reaction was incubated for 3 hours. The temperature was raised to about 25-30°C, and the reaction was maintained for 1 hour. Pump 25kg of ethyl acetate into the kettle to extract for the first time. After standing for 0.5 hours, the layers were separated, and the lower aqueous phase was taken for a second time with 15 kg of dichloromethane. The organic phases were combined and washed once with 10 kg of process water. After standing for 0.5 hours, 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 moisture content of 5% is used, and the yield is 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 moisture content of 3% is used, and the yield is 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 novel preparation method of 4-methyl-5-thiazole carboxaldehyde. Background technique [0002] Fodorant axetil is a third-generation oral cephalosporin antibiotic, which was developed by Meiji Fruit Company in Japan in 1994 for the treatment of infections caused by gram-positive and gram-negative bacteria, especially for grapes. Gram-positive bacteria of the genus Streptococcus, including Streptococcus pneumoniae, Escherichia coli, Branhamella catarrhalis, Klebsiella, Proteus, Haemophilus influenzae and other gram-negative bacteria And anaerobic bacteria such as Peptostreptococcus, Propionibacterium acnes, Bacteroides, etc., all show strong antibacterial power. my country approved the 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...

Claims

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Application Information

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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
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