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Benzisothiazolone derivatives and synthetic method thereof

A technology of benzisothiazolinone and synthesis method, which is applied in the field of drug synthesis, can solve the problems of biological resistance and the like, and achieves the effects of good biological activity, simple reaction operation and high reaction yield

Inactive Publication Date: 2015-09-23
胡俊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, long-term use of a single agent can easily lead to drug resistance. It is necessary to develop a more active, more stable, broader-spectrum, and less toxic fungicide through synthetic process design and drug structure innovation by drug synthesis scholars.

Method used

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  • Benzisothiazolone derivatives and synthetic method thereof
  • Benzisothiazolone derivatives and synthetic method thereof
  • Benzisothiazolone derivatives and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 4-Methylphenyl-1,2-benzisothiazolin-3-one-2-ylacetamide and its synthesis method

[0018] In a 250ml three-neck flask equipped with magnetic stirring, add 0.01mol of 4-methylaniline, 0.013mol of benzisothiazolinone acetic acid, add 0.012mol of HoBt and 0.012mol of EDCI as condensing agents, dissolve in DMF, and Reaction 20h. The reaction is complete. The solution was poured into water, and a large amount of solid precipitated out. Filtration, pickling, washing, drying, in crude products. Column chromatography gave 4-methylphenyl-1,2-benzisothiazolin-3-one-2-ylacetamide as a yellow solid, yield: 73%. Melting point: 159~160℃.

[0019]

[0020] 1 H NMR (DMSO-d6, 500MHz): 2.23 (S, 3H, CH 3 ), 5.11 (s, 2H, CH 2 ), 7.09-8.08 (m, 8H, H ring ), 10.11 (s, 1H, NH).

[0021] IR (cm -1 ): 3250, 3020, 1670, 1642, 1595, 1286, 1150, 648.

[0022] The bactericidal activity test shows that: when the compound concentration is 50ppm, the bacteriostatic rate of heterotrophic ...

Embodiment 2

[0024] 3-Chloro-1,2-benzisothiazolin-3-one-2-ylacetamide and its synthesis method

[0025] In a 250ml three-neck flask, add 0.01mol of 3-chloroaniline, 0.011mol of benzisothiazolinone acetic acid, and then add 0.011mol of HoBt and 0.013mol of EDCI as a condensation agent, dissolve completely with 15ml of DMSO, and react at room temperature for 16 hours. The reaction is complete. The solution was poured into water, and a large amount of solid precipitated out. Filtration, pickling, washing, drying, in crude products. Column chromatography gave 2-methoxyphenyl-1,2-benzisothiazolin-3-one-2-ylacetamide as a white solid, yield: 67%. Melting point: 176-177°C.

[0026]

[0027] 1 H NMR (DMSO-d6, 300MHz): 5.14(s, 2H, CH 2 ), 7.52-8.11 (m, 8H, H ring ), 10.28 (s, 1H, NH).

[0028] IR (cm -1 ): 3280, 3052, 1680, 1642, 1598, 1297, 1230, 1148, 648.

Embodiment 3

[0030] 2, 4 - Dimethylphenyl-1,2-benzisothiazolin-3-one-2-ylacetamide and its synthesis method

[0031] In a 250ml three-necked flask, 0.01mol of 2,4-dimethylaniline and 0.014mol of benzisothiazolinone acetic acid were added. Add 0.013 mol of HoBt and 0.011 mol of EDCI as a condensation agent, dissolve in DMSO, and react at room temperature for 24 hours. After the reaction was completed, the solution was poured into water, and a large amount of solids were precipitated. Filtration, pickling, washing, drying, in crude products. Column chromatography gave 2,4-dimethylphenyl-1,2-benzisothiazolin-3-one-2-ylacetamide as a yellow solid, yield: 72%. Melting point: 179-181°C.

[0032]

[0033] 1 H NMR (DMSO-d6, 300MHz): 3.31(s, 3H, CH 3 ), 5.14 (s, 2H, CH 2 ), 6.96-8.10 (m, 7H, H ring ), 9.54 (s, 1H, NH).

[0034] IR (cm -1 ): 3245, 3021, 1672, 1614, 1593, 1275, 1151, 648.

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Abstract

The invention discloses benzimidazole isothiazolinone amide derivatives and a synthetic method thereof; the series of compounds are compounds represented by the general formula (I), wherein R is 4-methyl, 3-chlorine or 2,4-dimethyl. The synthetic method is characterized by comprising the following steps: taking substituted aniline and benzisothiazolone acetic acid having the molar ratio of 1:(1-1.5), and taking HoBt and EDCI as condensing agents, wherein the molar ratio of substituted aniline to the condensing agent HoBt is (1:1.1)-(1:1.3), and the molar ratio of substituted aniline to the condensation agent EDCI is (1:1.1)-(1:1.3); completely dissolving the raw materials by an organic solvent, and carrying out a reaction for 16-24 h at room temperature; after completion of the reaction, pouring the solution into water, precipitating a large number of solids, filtering, pickling, washing with water, drying, and thus obtaining a crude product; and carrying out column chromatography to obtain the benzisothiazolone derivatives. The preparation process is easy to industrialize, and the target product has good biological activity.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a benzisothiazolinone derivative and a synthesis method thereof. Background technique [0002] Nitrogen-containing single heterocyclic compounds or fused heterocyclic compounds with special structures have attracted more and more attention from chemists due to their strong physiological activities, and have become a research hotspot in the field of drug synthesis. [0003] Heterocyclic compounds have good biological activity and can be used as fungicides, insecticides, plant growth regulators, etc., and can also be used as intermediates for the synthesis of pesticides, medicines and dyes. [0004] Isothiazolinone compounds are widely used in industry because of their strong antibacterial ability, small application dose, good compatibility, low toxicity, and strong antibacterial effect on various bacteria. Isothiazolinone is a general term for a class of derivatives. It w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/04A01P1/00A61P31/04
CPCC07D275/04
Inventor 胡俊
Owner 胡俊
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