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Method for generating benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in aqueous phase

A technology of benzisothiazolinone and compound, which is applied in the field of organic sulfur-nitrogen bond synthesis, can solve the problems of generating toxic waste, long reaction time, excessive additives, etc., and achieves less by-products, high reaction efficiency and environmental friendliness Effect

Active Publication Date: 2018-12-28
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, these methods have obvious disadvantages: generation of toxic waste, excessive additives, lengthy steps or long reaction times, etc.
And most of the existing reports used organic solvents

Method used

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  • Method for generating benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in aqueous phase
  • Method for generating benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in aqueous phase
  • Method for generating benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in aqueous phase

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation method of the benzisothiazolinone compound A of the following structural formula:

[0029]

[0030] In the 50mL flask, add 2g N-tert-butyl thiosalicylic acid amide, 0.1g (5wt%) Tetrasodium iron tetracarboxyphthalocyanine [FePc(CO 2 Na) 4 ], 0.02g (1wt%) tetracarboxy manganese phthalocyanine tetrasodium [MnPc(CO 2 Na) 4 ] and 30mL of water, poured into oxygen, heated to 100°C, and reacted for 2 hours. After the reaction, cooled, filtered, washed the filter cake with 20mL of water, and dried to obtain 1.9 g of white solid. The structure of the product was determined by NMR, MS and other methods as the target The yield of product A is 96%, and the purity of the product by liquid chromatography analysis is 99%.

[0031] 1 H NMR (600MHz, CDCl 3 ,SiMe 4 )δ: 7.96 (d, J = 7.8Hz, 1H), 7.59-7.49 (m, 2H), 7.36 (t, J = 7.4Hz, 1H), 1.71 (s, 9H);

[0032] 13 C NMR (150MHz, CDCl 3 ,SiMe 4 )δ: 165.5, 139.3, 131.3, 126.8, 126.0, 125.1, 119.7, 58.6, 28.3.

Embodiment 2

[0034] The preparation method of the benzisothiazolinone compound B of the following structural formula:

[0035]

[0036] In the 100mL flask, add 4g N-phenyl thiosalicylic acid amide, 0.08g cobalt tetrasodium tetrasulfonate phthalocyanine [CoPc(SO 3 Na) 4 ], 0.08g copper tetracarboxyphthalocyanine [CuPc(CO 2 h)4 ], 0.12g tetrasulfonic manganese phthalocyanine [MnPc(SO 3 h) 4 ] and 50mL water, poured into oxygen, heated to 80°C, reacted for 12h, after the reaction was finished, cooled, filtered, washed the filter cake with 40mL water, dried to obtain 3.1g target product B, the yield was 78%, liquid chromatography analysis The product purity is 99%.

Embodiment 3

[0038] The preparation method of the benzisothiazolinone compound C with the following structural formula:

[0039]

[0040] In the 250mL flask, add 10g N-(2-methyl) phenyl thiosalicylic acid amide, 0.1g tetrapotassium tetrasulfonic manganese phthalocyanine [MnPc(SO 3 K) 4 ] and 100mL water, poured into oxygen, heated to 90°C, reacted for 24h, after the reaction was finished, cooled, filtered, washed the filter cake with water, dried to obtain 8.2g target product C, the yield was 82%, and the product was analyzed by liquid chromatography The purity is 99%.

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Abstract

The invention provides a method for synthesizing benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in an aqueous phase. A water-soluble transition metal phthalocyanine compound is taken as a catalyst, and a thiosalicylic acid amide compound reacts in the aqueous phase for 2 to 24h at the temperature of 80 to 100 DEG C in an oxygen environment to generate the benzisothiazolinone compounds. The reaction is carried out in the aqueous phase without adding other organic solvents; the catalyst has high catalytic activity and high reaction efficiency; the method for generating the benzisothiazolinone compounds by catalyzing the oxidization of the molecular oxygen in the aqueous phase is simple in synthesis process, high in product selectivity and less in by-products andwaste and environment-friendly, and further has a stronger industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of organic sulfur-nitrogen bond synthesis, in particular to a method for synthesizing benzisothiazolinone compounds by catalyzing molecular oxygen oxidation in water phase. Background technique [0002] Benzisothiazolinone derivatives are a very important class of organic heterocyclic compounds, which play an important role in medicine, agriculture, food science and industrial production [Craine, L.; Raban, M.Chem.Rev.1989 , 89, 689-712]. Since the first synthesis of benzisothiazolinones by Mckibben and McClelland in 1923 [McKibben, M.; McClelland, E.W. J. Chem. Soc., Trans. 1923,123,170-173], researchers have found Drugs have a broad spectrum of biological activities, such as antibacterial, antipsychotic, antiviral, antithrombotic, analgesic, etc. [Jorgensen, W.L.; Trofimov, A.; Du, X.; et al.Biorg.Med.Chem.Lett. 2011, 21, 4545-4549]. Now it is widely used as the main component of preservatives in our da...

Claims

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Application Information

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IPC IPC(8): C07D275/04C07D417/04
CPCC07D275/04C07D417/04
Inventor 杨贯羽杨利婷袁冰芯
Owner ZHENGZHOU UNIV
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