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Method for preparing compound of 5-substitution-3-amido isoxazole

A technology for isoxazole compounds and aminoisoxazoles is applied in the field of preparation of 5-substituted-3-aminoisoxazole compounds, which can solve the problem of increasing difficulty in separation and purification of target products, affecting promotion and use, and reducing the yield of target products. and other problems, to achieve the effects of easy temperature control, increased yield, and mild reaction conditions

Inactive Publication Date: 2005-01-12
SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] It can be seen that adopting this preparation method will lead to the generation of by-product 5-amino-3-tert-butylisoxazole compound and its ketone compound, which not only reduces the productive rate of target product, but also increases the separation and purification of target product simultaneously. difficulty
The above shortcomings have seriously affected the further promotion and use of this method.

Method used

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  • Method for preparing compound of 5-substitution-3-amido isoxazole
  • Method for preparing compound of 5-substitution-3-amido isoxazole
  • Method for preparing compound of 5-substitution-3-amido isoxazole

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of 5-methyl-3-aminoisoxazole compound

[0029] Include the following steps:

[0030] Weigh the material by the following weight percentages: the weight percentages of methyl acetoacetonitrile, sodium hydroxide, hydroxylamine hydrochloride and water are respectively: 6.2%: 3.2%: 4.6%: 76%, the reaction temperature of control system is 50- 55°C;

[0031] Add 15ml of CCl to the above reaction product 4 , and then transferred to a 150ml separatory funnel, shaken for extraction, left to stand for layers, the lower layer of CCl 4 Layer is a yellowish brown liquid, the upper water layer is a light yellow liquid, reclaim CCl 4 Layer, collect the water layer in the reactor;

[0032] Adjust the pH value of the above collected solution to 5.0-6.0, adjust the temperature at 50-55°C, stir and react for 2 hours, after a small amount of crystal grains are precipitated, cool and stand still;

[0033] Adjust the pH value to 9-13, a large amount of prec...

Embodiment 2

[0035] Embodiment 2: Synthesis of 5-tert-butyl-3-aminoisoxazole compound

[0036] Include the following steps:

[0037] Weigh the material by the following weight percentages: the weight percentages of tert-butylacetoacetonitrile, sodium hydroxide, hydroxylamine hydrochloride and water are respectively: 7.5%: 2.7%: 4.6%: 85.2%, the reaction temperature of control system is 50 -60°C;

[0038] step is the same as in example 1, the difference is that CCl 4 Change the volume to 20ml;

[0039] Adjust the pH value of the above collected solution to 5.0-5.5, adjust the temperature at 50-60°C, stir and react for about 1 hr, a small amount of crystal grains precipitate, cool and stand still;

[0040] Adjust the pH value to 8-12, and a large amount of precipitates are formed. After filtering, washing and drying, a light yellow crystalline solid is obtained.

[0041] Melting point: 108-110°C; yield 82%

Embodiment 3

[0042] Embodiment 3: Synthesis of 5-methyl-3-aminoisoxazole compound

[0043] Include the following steps:

[0044] weighing material by following weight percentage: the percentage by weight of methyl acetoacetonitrile, potassium hydroxide, hydroxylammonium sulfate and water is respectively: 6.5%: 3.0%: 5.5%: 85%, the reaction temperature of control system is 45- 55°C;

[0045] step is the same as in example 1, the difference is that CCl 4 Change the volume to 10ml;

[0046] Adjust the pH value of the above collected solution to 4.5-5.0, adjust the temperature at 45-55°C, stir and react for 1.5hr, a small amount of crystal grains precipitate, cool and stand;

[0047] Adjust the pH value to 10-12, and a large amount of precipitates are formed. After filtering, washing and drying, a light yellow crystalline solid is obtained.

[0048] Yield 80%.

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Abstract

In this invention, said product has its structural formula as shown, where: C=carbon, R=1-4 alkyl. Substituled acetyl acetonitrile reacts with oxammonium hydrochloride in weak alkaline condition to obtain amino oxime and side-product 5-amino-3-substituted isooxazole compound mixture. Then, its extracted by solvent to rmove side-product. Amino oxime proceeds cyclization in weak acid condition to obtain final product-5-substituted-3-amino-isooxazole with high pureness.

Description

Technical field: [0001] The invention relates to an azo dye and a metal chelate thereof, in particular to a preparation method of a 5-substituted-3-aminoisoxazole compound. The compound of the invention is one of the important precursors for synthesizing novel short-wavelength (350nm-400nm) azo dyes containing isoxazole rings and metal chelates thereof. Background technique: [0002] At present, azo dyes and their metal chelates are hot spots in the development of organic optical storage materials, especially the continuous blue shift of the working wavelength of lasers used for optical storage, requiring the development of short wavelengths that can match the working wavelengths of short wavelength lasers Azo dyes and their metal chelates have become the focus of research on these compounds. Recent studies have shown that the absorption spectra of azo dyes and their metal chelates are related to their molecular skeletons. According to different skeletons, azo dyes and thei...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/14
Inventor 黄福新吴谊群顾冬红干福熹
Owner SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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