Benzisothiazolinone isoxazole acetamide derivative, synthesis method and application thereof

A technology of benzisothiazolinone acetic acid and benzisothiazolinone, which is applied in the field of benzisothiazolinone isoxazole acetamide derivatives and their synthesis, can solve the problems of lack of independent innovation and achieve reaction Mild conditions, simple reaction operation, and high reaction yield

Active Publication Date: 2019-03-29
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, my country's pesticide and pharmaceutical industries are mainly based on the imitation of foreign drugs, lacking independent innovation

Method used

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  • Benzisothiazolinone isoxazole acetamide derivative, synthesis method and application thereof
  • Benzisothiazolinone isoxazole acetamide derivative, synthesis method and application thereof
  • Benzisothiazolinone isoxazole acetamide derivative, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Synthesis of 2-(benzisothiazolin-3-one-2-yl)-N-(3-phenylisoxazol-5-yl)acetamide

[0027] In a 100ml four-necked flask, 3-phenyl-5-aminoisoxazole and benzisothiazolin-3-one-2-ylacetic acid were reacted in a molar ratio of 1:1.1, and DMF(N,N- Dimethylformamide) can be dissolved, add HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride], HOBT , The molar ratio of EDCI to 3-phenyl-5-aminoisoxazole is 1:1:1, react at 25°C for 26h, and the reaction is completed. The solution was poured into water, and a large amount of solid precipitated out. Filtration, alkali washing, acid washing, water washing. After drying, the crude product was obtained, and the target compound was obtained by column chromatography (ethyl acetate:petroleum ether=1:1.1). Yield: 68.5%. Melting point: 189~191℃. The structural formula and spectrum analysis of the product are as follows:

[0028]

[0029] 1 H NMR (DMSO-d6, 300MHz): 5.27(s,2H...

Embodiment 2

[0036] Synthesis of 2-(Benzisothiazolin-3-on-2-yl)-N-(3-(2-chlorophenyl)isoxazol-5-yl)acetamide

[0037] In a 100ml four-necked flask, 3-o-phenylchloro-5-aminoisoxazole and benzisothiazolin-3-ketone-2-ylacetic acid were reacted in a molar ratio of 1:1.2, with DMF (N, N-dimethylformamide) can be dissolved, add HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride] , The molar ratio of HOBT, EDCI and 3-o-phenylchloro-5-aminoisoxazole is 1.3:1.2:1, react at 20°C for 30h, and the reaction is completed. The solution was poured into water, and a large amount of solid precipitated out. Filtration, alkali washing, pickling, water washing. After drying, a crude product was obtained, and the target compound was obtained by column chromatography (ethyl acetate:petroleum ether=1:1.3). Yield: 65.2%. Melting point: 174-175°C. The structural formula and spectrum analysis of the product are as follows:

[0038]

[0039] 1H NMR (DMSO-d6,...

Embodiment 3

[0046] Synthesis of 2-(Benzisothiazolin-3-on-2-yl)-N-(3-(4-fluorophenyl)isoxazol-5-yl)acetamide

[0047] In a 100ml four-necked flask, 3-p-fluorophenyl-5-aminoisoxazole and benzisothiazolin-3-ketone-2-ylacetic acid were reacted in a molar ratio of 1:1.2, with DMF (N, N-dimethylformamide) can be dissolved, add HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride] , the molar ratio of HOBT, EDCI and 3-p-fluorophenyl-5-aminoisoxazole is 1.4:1.1:1, react at 25°C for 32h, and the reaction is completed. The solution was poured into water, and a large amount of solid precipitated out. Filtration, alkali washing, acid washing, water washing. After drying, a crude product was obtained, and the target compound was obtained by column chromatography (ethyl acetate:petroleum ether=1:1.3). Yield: 65.2%. Melting point: 174-175°C. The structural formula and spectrum analysis of the product are as follows:

[0048]

[0049] 1 H NMR (DMS...

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Abstract

The invention discloses a benzisothiazolinone isoxazole acetamide derivative, a synthesis method and application thereof. The preparation method includes: reacting benzisothiazolinone acetic acid with3-substituted phenyl-5-aminoisoxazole in a mole ratio of 1:(1-1.5), performing dissolution with an organic solvent, adding HOBT(1-hydroxybenzotriazole) and EDCI[1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride as the condensing agent, with the HOBT(1-hydroxybenzotriazole), EDCI[1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 3-substituted phenyl-5-aminoisoxazole being in a mole ratio of (1-1.3):(1-1.5):1, and carrying out reaction at 10-30DEG C for 16-40h. The benzisothiazolinone isoxazole acetamide derivative has good inhibitory activity on seawater heterotrophic bacteria, and can achieve a highest inhibition rate up to 100%. The inhibitory effect on China chlorella and mussel is higher than that of 20% benzisothiazolinone-3-one (BIT) bactericide on the market,and the corrosion inhibition effect on carbon steel can reach 43.1%.

Description

technical field [0001] The invention relates to a benzisothiazolinone isoxazole acetamide derivative and a synthesis method and application thereof. Background technique [0002] The development of heterocyclic chemistry has brought the creation of functional compounds into an efficient era. Most heterocyclic compounds have good biological activity, especially those containing nitrogen, oxygen, and sulfur or fused heterocyclic compounds with special structures. Compounds, such as isoxazoles, pyrazoles, thiazoles, etc., have always been a research hotspot in the field of new drug creation because of their superior biological activity. [0003] Isoxazole and its isoxazole compounds are five-membered heterocyclic rings containing oxygen and nitrogen, which have good biological activity. They are not only important synthetic intermediates in organic synthesis, but also a number of isoxazole derivatives have been developed into Herbicides, fungicides, insecticides, in addition, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A01N43/80A01P1/00A01P3/00A01P9/00A01P13/00C02F1/50
CPCA01N43/80C02F1/50C02F2303/04C02F2303/08C07D417/12
Inventor 于鹏刘璧铭潘建李溪徐炎华
Owner NANJING UNIV OF TECH
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