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1,3,4-thiadiazole benzisothiazolinone acetamide derivative and synthesis method thereof

A technology of isothiazolinone acetamide and thiadiazolebenzene, applied in the field of 1,3,4-thiadiazole benzisothiazolinone acetamide derivatives and their synthesis, which can solve the problems of lack of independent innovation , to achieve the effects of mild reaction conditions, high reaction yield, and simple reaction operation

Active Publication Date: 2014-05-07
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • 1,3,4-thiadiazole benzisothiazolinone acetamide derivative and synthesis method thereof
  • 1,3,4-thiadiazole benzisothiazolinone acetamide derivative and synthesis method thereof
  • 1,3,4-thiadiazole benzisothiazolinone acetamide derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of 2-(Benzisothiazolin-3-on-2-yl)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-acetamide

[0021] In a 250ml four-necked flask, 2-amino-5-substituted phenyl-1,3,4 thiadiazole and benzisothiazolin-3-one-2-ylacetic acid were reacted in a molar ratio of 1:1.1, Just dissolve it with DMF (N,N-dimethylformamide), add HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiethylene Amine hydrochloride], the molar ratio of it to 2-amino-5-substituted phenyl-1,3,4-thiadiazole is 1:1:1, react at 25°C for 16h, 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). Yield: 76%. Melting point: 238-239°C. The structural formula and spectrum analysis of the product are as follows:

[0022]

[0023...

Embodiment 2

[0027] Synthesis of 2-(benzisothiazolin-3-on-2-yl)-N-(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)-acetamide

[0028] In a 250ml four-neck flask, react 2-amino-5-m-benzyl-1,3,4thiadiazole and benzisothiazolin-3-one-2-ylacetic acid, the molar ratio is 1:1.5 , dissolve it with DMSO (dimethyl sulfoxide), add HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride salt], the molar ratio of 2-amino-5-substituted phenyl-1,3,4-thiadiazole is 1.1:1.3:1, react at 20°C for 20h, 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: 82%. Melting point: 217~218℃. The structural formula and spectrum analysis of the product are as follows:

[0029]

[0030] 1 H NMR (DMSO-d6, 300MHz)...

Embodiment 3

[0034] N-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-(benzisothiazolin-3-one-2-yl)-acetamide Synthesis

[0035] In a 250ml four-necked flask, 2-amino-5-p-benzyloxy-1,3,4 thiadiazole and benzisothiazolin-3-one-2-ylacetic acid were reacted in a molar ratio of 1: 1.1, just dissolve with DMF (N,N-dimethylformamide), add HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbon diimine hydrochloride],

[0036] The molar ratio to 2-amino-5-substituted phenyl-1,3,4-thiadiazole is 1:1.1:1, react at 25°C for 18h, and the reaction is complete. 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). Yield: 71%. Melting point: 239-241°C. The structural formula and spectrum analysis of the product are as follows:

[0037]

[0038]...

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Abstract

The invention relates to a 1,3,4-thiadiazole benzisothiazolinone acetamide derivative and a synthesis method thereof. The 1,3,4-thiadiazole benzisothiazolinone acetamide derivative has a structural formula shown in a drawing, wherein R is hydrogen, 3-methyl, 4-methoxy, 4-chloro or 2-bromo-4-nitro. The synthesis method comprises the steps of dissolving substituted 2-amino-5-substituted phenyl-1,3,4-thiadiazole and benzisothiazolin-3-one-2-yl acetic acid with an organic solvent, adding a condensing agent, reacting for 16-24 hours at the temperature of 10-30 DEG C, pouring a solution into water after the reaction is completed, and precipitating solids; filtrating, washing, drying, and then carrying out column chromatography, thereby obtaining the 1,3,4-thiadiazole benzisothiazolinone acetamide derivative which has good biological activity. According to the 1,3,4-thiadiazole benzisothiazolinone acetamide derivative and the synthesis method thereof, the reaction conditions are mild, the reacting operation is simple and convenient, and the reaction yield is relatively high.

Description

technical field [0001] The invention relates to a 1,3,4-thiadiazole benzisothiazolinone acetamide derivative and a synthesis method thereof. Background technique [0002] Nitrogen-containing heterocyclic compounds usually have unique biological activity, low toxicity and high systemic property, and are often used as structural units of medicines and pesticides. Nitrogen-containing heterocyclic compounds are easy to carry out structural modification, and various functional groups can be conveniently introduced. [0003] Thiadiazoles are a widely studied class of nitrogen-containing heterocyclic compounds. In terms of pesticides, it can be used as fungicides, herbicides, plant growth regulators and insecticides, and is also widely used in the field of medicine. Thiadiazoles are often used as drug intermediates, among which 1,3,4-thiadiazoles are the most common and widely used. [0004] Isothiazolinone compounds are a new type of high-efficiency broad-spectrum fungicides, w...

Claims

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Application Information

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IPC IPC(8): C07D417/12A01P1/00
CPCC07D417/12
Inventor 徐炎华于鹏万嵘郑善龙胡俊李溪
Owner NANJING UNIV OF TECH
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