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Preparation method of N-(2-methylthiophenyl)isoindole-1,3-diketone compound

A technology of methylthiophenyl and compound, which is applied in the field of preparing N-isoindole-1,3-dione compound, can solve the problems of metal palladium catalyst poisoning, toxicity, and difficult synthesis of compounds, and achieve easy-to-obtain, The effect of simple operation and simple process

Active Publication Date: 2018-06-22
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although there are currently many N -(2-methylthiophenyl) the preparation method of isoindole-1,3-diketone compound, but adopt these methods to be difficult to prepare the isoindole compound of sulfur-containing group, this is due to N -(2-Methylthiophenyl)isoindole-1,3-dione compound structure, the strong coordination ability of sulfur atom makes the metal palladium catalyst poisoned, which makes it difficult to synthesize such compounds
The carbonyl source used in traditional methods is mostly CO, which is extremely toxic and difficult to control in the reaction

Method used

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  • Preparation method of N-(2-methylthiophenyl)isoindole-1,3-diketone compound

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preparation example Construction

[0025] The invention discloses a N- (2-methylthiophenyl) the preparation method of isoindole-1,3-dione derivative, comprises the following steps: with N -(2-Methylthiophenyl)benzamide and sodium trifluoromethanesulfinate are the reaction substrates, and the molar ratio of the two is 1:2~1:3. By adding 10-20 mol% of palladium trifluoroacetate or palladium acetate as a catalyst, 100%-120 mol% of copper trifluoromethanesulfonate or copper tetrafluoroborate as one of the oxidants, in chlorobenzene or 1, 2-dichloroethane in one of the reaction solvents, reacted at a temperature of 120°C for 24 h; the chemical reaction formula is as follows:

[0026]

[0027] The -R is hydrogen, 2-methyl, 4-methyl, 3-methyl, 3,5-dimethyl, 4-ethyl, 4-methoxy, 3-methoxy, 3,4 -Methylenedioxy, 4-fluoro, 3-fluoro, 4-chloro, 3-chloro, 4-bromo, 4-iodo, 4-trifluoromethoxy, 4-trifluoromethyl, 4-phenyl , one of 2-naphthyl,

[0028] After the reaction is completed, after cooling, the reaction solution i...

specific Embodiment 1

[0029] Specific embodiment one: 48.6 milligrams (0.2 mmol) N -(2-Methylthiophenyl)benzamide, 87 mg (0.54 mmol) sodium trifluoromethanesulfinate, 17 mg (0.04 mmol) palladium trifluoroacetate, 86.7 mg (0.24 mmol) trifluoromethanesulfonic acid Copper, add 2 mL of chlorobenzene solvent. Reacted at room temperature at 120°C for 24 hours, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove the solvent, and the residue was subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 10:1, The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined, and the solvent was distilled off by a rotary evaporator, and dried in vacuo to obtain 41.4 mg of a white solid. - (2-Methylthiophenyl)isoindole-1, 3-dione, yield 77%. White solid. m.p. 158-160 o c. 1 H NMR (500 MHz, CDCl 3) δ 7.97 - 7.96 (m, 2H), 7.81 - 7.7...

specific Embodiment 2

[0030] Specific embodiment two: 51.4 milligrams (0.2 mmol) 2-methyl- N -(2-Methylthiophenyl)benzamide, 87 mg (0.54 mmol) sodium trifluoromethanesulfinate, 17 mg (0.04 mmol) palladium trifluoroacetate, 86.7 mg (0.24 mmol) trifluoromethanesulfonic acid Copper, add 2 mL of chlorobenzene solvent. Reacted at room temperature at 120°C for 24 hours, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove the solvent, and the residue was subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 10:1, The effluent was collected according to the actual gradient, detected by TLC, the effluent containing the product was combined, and the solvent was distilled off by a rotary evaporator, and the residue was chromatographed on a silica gel column, washed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 10:1 , collect the effluent according to the actu...

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Abstract

The invention discloses a preparation method of an N-(2-methylthiophenyl)isoindole-1,3-diketone compound. The preparation method comprises the following steps: by taking N-(2-methylthiophenyl)benzamide as a substrate; adding sodium trifluoromethanesulfinate into the substrate as a carbonyl source; adding a catalyst and carrying out stirred reaction in a reaction solvent for 24h under normal pressure and at 120 DEG C; after reaction is finished, filtering a reaction solution to obtain filtrate; concentrating the filtrate and removing the solvent by utilizing the rotary evaporator, so as to obtain residues; carrying out chromatography on the residues through a silica gel column; eluting through an eluting solution and collecting effluent liquid according to an actual gradient; combining theeffluent liquid containing a product, concentrating the combined effluent liquid and removing the solvent; finally, drying in vacuum to obtain a target product. The preparation method disclosed by theinvention has the advantages of simple preparation technology, less pollution, low energy consumption and high yield.

Description

technical field [0001] The present invention relates to the technical field of isoindole 1, 3-diketone compounds, especially a kind of preparation N -(2-Methylthiophenyl)isoindole-1,3-dione compound method. Background technique [0002] Isoindolinone and its derivatives are extremely important heterocyclic compounds, which widely exist in natural products and are important components of many medicines. Isoindolinone and its derivatives have a wide range of biological activities, such as antibacterial properties, anticancer antibiotics, and anticancer properties. Some of their derivatives can also be used as anti-Alzheimer's disease and anti-prostate cancer drugs. Therefore, chemists have developed various methods for constructing isoindolinone compounds. [0003] When chemists construct isoindolinone compounds, the most direct method is to use 2-halogenated benzylamine and 2-halogenated benzaldehyde as raw materials, and under palladium catalysis, CO is bubbled into the re...

Claims

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Application Information

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IPC IPC(8): C07D209/48
CPCC07B2200/07C07D209/48
Inventor 张小红施林峰张兴国胡伯伦邓辰亮
Owner WENZHOU UNIVERSITY
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