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Method for preparing 2-aldehyde oxazole

A technology of aldooxazole and oxazole, which is applied in the field of preparation of 2-aldooxazole, can solve the problems of unsuitable storage and transportation, cumbersome post-processing, and low yield, and achieve convenient storage and transportation, and simple post-processing methods , The effect of stable process conditions

Active Publication Date: 2014-04-16
LIAONING ASYMCHEM LAB CO LTD
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AI Technical Summary

Problems solved by technology

[0003] At this stage, the method for preparing 2-formyl oxazole is mainly the organolithium reagent method. First, the lithiation reaction of oxazole and organolithium occurs, and then reacts with N,N-dimethylformamide or N-formylmorpholine On the aldehyde group, the post-treatment of these two methods is relatively cumbersome. The method of using N,N-dimethylformamide on the aldehyde group needs to obtain the product through silica gel column chromatography. Because the product has a low boiling point and high water solubility The characteristics of this method lead to a very low yield. This method is not suitable for large-scale production. The product obtained is an oily mixture by using the method of N-formylmorpholine reaction on the aldehyde group, and the pure compound of the product cannot be obtained, and it is not suitable for for storage and transport

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  • Method for preparing 2-aldehyde oxazole
  • Method for preparing 2-aldehyde oxazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: a kind of method for preparing 2-formyl oxazole is characterized in that concrete steps are as follows:

[0026] (1) Feeding: Add 20.0kg of main raw material oxazole into the 1500L reactor 600L tetrahydrofuran, start stirring;

[0027] (2) Add n-butyllithium solution dropwise: cool the system down to -65±5°C, and add 24.1kg of n-butyllithium solution dropwise at -65±5°C, after dropping, keep warm at -65±5°C 5h;

[0028] (3) Add N-formylpiperidine dropwise: Add 163.8kg N-formylpiperidine dropwise to the system at -65±5°C, after the drop is complete, the system is warmed to 25±5°C and kept at 20±5°C for 50 hours ;

[0029] (4) Post-treatment: Cool the system to 0±3°C, stir and crystallize, filter with suction, rinse the filter cake with 80L methyl tert-butyl ether, and dry it under nitrogen protection to obtain solid lithium salt NMR internal standard purity (NMR): 98.8%, yield 85.0%;

[0030] (5) Hydrolysis: To the solid lithium salt obtained in step...

Embodiment 2

[0032] Embodiment 2: a kind of method for preparing 2-formyl oxazole is characterized in that concrete steps are as follows:

[0033] (1) Feeding: Add 6.5kg of the main raw material oxazole and 227.5L of methyl tert-butyl ether into the 500L reactor, and start stirring;

[0034] (2) Add n-butyllithium solution dropwise: cool the system to -85±5°C, and add 7.2kg of n-butyllithium solution dropwise at -85±5°C, after dropping, keep warm at -85±5°C 5h;

[0035] (3) Adding N-formylpiperidine dropwise: Add 106.5kg N-formylpiperidine dropwise to the system at -85±5°C, after the drop is complete, the system is warmed to 25±5°C and kept at 25±5°C for 48 hours ;

[0036] (4) Post-treatment: Cool the system to 0±3°C, stir and crystallize, filter with suction, rinse the filter cake with 80L methyl tert-butyl ether, and dry it under nitrogen protection to obtain solid lithium salt NMR internal standard purity (NMR): 98.2%, yield 80.5%;

[0037] (5) Hydrolysis: Add dropwise 65L of dilu...

Embodiment 3

[0038] Embodiment 3: a kind of method for preparing 2-formyl oxazole is characterized in that concrete steps are as follows:

[0039] (1) Feeding: Add 2.8kg of main raw materials oxazole and 20L tetrahydrofuran into a 100L reaction bottle, and start stirring;

[0040](2) Add n-butyllithium solution dropwise: cool the system down to -65±5°C, and add 2.8kg of n-butyllithium solution dropwise at -65±5°C, after dropping, keep warm at -65±5°C 2h;

[0041] (3) Adding N-formylpiperidine dropwise: Add 4.6kg N-formylpiperidine dropwise to the system at -65±5°C, after the drop is complete, the system is warmed to 25±5°C and kept at 25±5°C for 32 hours ;

[0042] (4) Post-treatment: Cool the system to 0±3°C, stir and crystallize, filter with suction, rinse the filter cake with 2.8L methyl tert-butyl ether, and dry it under nitrogen protection to obtain solid lithium salt. (NMR): 98.5%, yield 75.0%;

[0043] (5) Hydrolysis: Add 5.6L of 20% dilute acetic acid solution dropwise to the s...

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Abstract

The invention relates to a method for preparing 2-aldehyde oxazole, comprising the steps of selecting commercial material on the market or easily-prepared oxazole as original raw material; dropping n-butyllithium to the organic phase solution of the main material oxazole at low temperature; and adding N-formoxyl piperidine to the reaction system, and obtaining solid lithium salt with high nuclear magnetic purity. The nuclear magnetic purity is higher than 98.0% stably and the yield is 75.0-85.0%. The synthetic method for obtaining 2-aldehyde oxazole by diluted acid hydrolysis has stable process condition, moderate chemical reaction conditions, simple operation and low pollution during the whole production and provides a new idea and a method for preparing 2-aldehyde oxazole.

Description

(1) Technical field: [0001] The invention relates to a method for preparing oxazole compounds, in particular to a method for preparing 2-formyl oxazole. (2) Background technology: [0002] Oxazole is a five-membered ring containing O and N atoms in the 1 and 3 positions. It is a liquid with a pyridine-like odor and is easily soluble in water. It is a very stable compound. It is very stable in hot strong acids and does not undergo self-oxidation. reaction and does not participate in any normal biochemical process. Oxazole compounds are an important class of heterocyclic compounds. Some compounds with oxazole rings have biological activity, and they are also widely used in intermediates and drug synthesis. Oxazole-2-carboxaldehyde is to increase an aldehyde group substitution on the oxazole ring, which increases the reactivity of oxazole, and can be synthesized by a conventional biochemical process to have a biologically active compound with an oxazole ring. In intermediates,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/32
Inventor 洪浩卢江平汪胜华
Owner LIAONING ASYMCHEM LAB CO LTD
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