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Preparation technology for 3-aryl-4-nitro isoxazole compound

A technology of nitroisoxazole and preparation process, which is applied in directions such as organic chemistry, can solve the problems of high production cost, difficult separation of reaction by-products, and difficulty in obtaining raw materials, and achieves easy product, mild and easy-to-control operating conditions, and low cost of raw materials. Inexpensive effect

Inactive Publication Date: 2017-11-24
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has solved the problems that the raw materials are not easy to obtain, the reaction by-products are difficult to separate, and the production cost is high in the existing process.

Method used

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  • Preparation technology for 3-aryl-4-nitro isoxazole compound
  • Preparation technology for 3-aryl-4-nitro isoxazole compound
  • Preparation technology for 3-aryl-4-nitro isoxazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Preparation of 3-(4-bromophenyl)-4-nitroisoxazole

[0017] A. Preparation of p-bromobenzaldehyde oxime

[0018] In a single-necked flask, dissolve p-bromobenzaldehyde (10.0g, 54.0mmol), hydroxylamine hydrochloride (4.9g, 70.5mmol) and anhydrous sodium acetate (8.9g, 108.5mmol) in ethanol (100mL), and react at 45°C for 1h . After the reaction was completed, cool to room temperature, filter with suction, wash the filter cake with ethanol (50mL×3), combine the filtrates, evaporate the solvent to dryness under reduced pressure, dissolve the residue with ethyl acetate (100mL), wash with pure water (100mL×2), and remove Dry over sodium sulfate, evaporate the solvent under reduced pressure to obtain 10.0 g of p-bromobenzaldehyde oxime as a white solid, with a yield of 92.8%.

[0019] B. Preparation of Chloroxime

[0020] In a three-neck flask, p-bromobenzaldehyde oxime (5 g, 25.0 mmol) was dissolved in N,N-dimethylformamide (100 mL), NCS (3.3 g, 25.0 mmol) was add...

Embodiment 2

[0026] Example 2 Preparation of 3-(3-bromophenyl)-4-nitroisoxazole

[0027] A. Preparation of m-bromobenzaldehyde oxime

[0028] In a single-necked flask, dissolve m-bromobenzaldehyde (10.0g, 54.0mmol), hydroxylamine hydrochloride (4.9g, 70.5mmol) and anhydrous sodium acetate (8.9g, 108.5mmol) in ethanol (100mL), and react at 45°C for 1h . After the reaction was completed, cool to room temperature, filter with suction, wash the filter cake with ethanol (50mL×3), combine the filtrates, evaporate the solvent to dryness under reduced pressure, dissolve the residue with ethyl acetate (100mL), wash with pure water (100mL×2), and remove Dry over sodium sulfate, and distill off the solvent under reduced pressure to obtain 9.8 g of m-bromobenzaldehyde oxime as a white solid, with a yield of 90.8%.

[0029] B. Preparation of Chloroxime

[0030] In a three-necked flask, m-bromobenzaldoxime (5 g, 25.0 mmol) was dissolved in N,N-dimethylformamide (100 mL), NCS (3.3 g, 25.0 mmol) was ad...

Embodiment 3

[0036] Example 3 Preparation of 3-(2-bromophenyl)-4-nitroisoxazole

[0037] A. Preparation of o-bromobenzaldehyde oxime

[0038] In a single-necked flask, dissolve o-bromobenzaldehyde (10.0g, 54.0mmol), hydroxylamine hydrochloride (4.9g, 70.5mmol) and anhydrous sodium acetate (8.9g, 108.5mmol) in ethanol (100mL), and react at 45°C for 1h . After the reaction was completed, cool to room temperature, filter with suction, wash the filter cake with ethanol (50mL×3), combine the filtrates, evaporate the solvent to dryness under reduced pressure, dissolve the residue with ethyl acetate (100mL), wash with pure water (100mL×2), and remove Dry over sodium sulfate, evaporate the solvent under reduced pressure to obtain 10.1 g of o-bromobenzaldoxime as a white solid, with a yield of 93.4%.

[0039] B. Preparation of Chloroxime

[0040] In a three-neck flask, o-bromobenzaldoxime (5 g, 25.0 mmol) was dissolved in N,N-dimethylformamide (100 mL), NCS (3.3 g, 25.0 mmol) was added in batche...

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Abstract

The invention discloses a preparation technology for a 3-aryl-4-nitro isoxazole compound. The preparation technology comprises the following steps: synthesizing a compound shown as formula II through the nucleophilic addition of hydroxylamine hydrochloride and the compound shown as formula I used as the raw material; acquiring the compound shown as formula III through the substitution reaction of the compound shown as formula II and N-chlorosuccinimide; preparing 1-dimethyl amino-2-nitro ethylene through the reaction of N,N-dimethylformamide dimethyl acetal and nitromethane used as the raw material; and acquiring a target product 3-aryl-4-nitro isoxazole compound through the cyclization reaction of the compound shown as formula III and 1-dimethyl amino-2-nitro ethylene. The raw materials in the synthesis route are low in cost and easily acquired, the operation condition is mild and is easily controlled, the product is easily purified and the preparation technology is a new method for synthesizing the 3-aryl-4-nitro isoxazole compound.

Description

technical field [0001] The invention relates to a preparation process of a 3-aryl-4-nitroisoxazole compound. It belongs to the field of organic synthesis, fine chemical industry and pharmaceutical intermediates. Background technique [0002] Isoxazole and its derivatives are a class of five-membered heterocyclic compounds containing nitrogen and oxygen. They are easy to form hydrogen bonds with other compounds and coordinate with metal ions. They are important pharmacologically active monomers and intermediates in organic synthesis. It is also an important structural unit of natural products, widely used in organic synthesis, medicine, pesticides, dyes and other aspects. In medicine, isoxazole compounds have anti-cold, anti-cancer, hypoglycemic, analgesic, anti-inflammatory and other effects, and can be used as antifungal agents, antibacterial agents, cyclooxygenase (COX-2) inhibitors and human immunodeficiency Virus (HIV) inhibitors, etc. In terms of pesticides, isoxazol...

Claims

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Application Information

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IPC IPC(8): C07D261/14
CPCC07D261/14
Inventor 乐意周志旭赵春深
Owner GUIZHOU UNIV
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