A kind of indenone with trifluoromethylthio group and its derivatives and preparation method thereof

A technology of trifluoromethylthio and derivatives, applied in sulfide preparation, organic chemistry and other directions, can solve the problems of high cost and poor substrate adaptability, and achieve the effects of low cost, short reaction time and high atom economy

Active Publication Date: 2017-12-26
瑞安宝源化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the deficiencies of the prior art, the present invention provides an environmentally friendly, safe and efficient preparation method for preparing indanone with trifluoromethylthio and its derivatives. The preparation method solves the problem of directly generating indanones There are technical problems such as high cost and poor substrate adaptability in the process of compounding; and the preparation method has many advantages such as low cost, high stability, mild reaction conditions, short reaction time, cheap and easy-to-obtain raw materials, and high product yield and purity. advantage

Method used

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  • A kind of indenone with trifluoromethylthio group and its derivatives and preparation method thereof
  • A kind of indenone with trifluoromethylthio group and its derivatives and preparation method thereof
  • A kind of indenone with trifluoromethylthio group and its derivatives and preparation method thereof

Examples

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specific example 1

[0084] Specific example one: Synthesis of 3-(4-(methyl)benzene) using 3-(4-(methyl)benzene)-1-phenylprop-2-yn-1-ketone and silver trifluoromethanethiolate -2-((trifluoromethyl)thio)-1H-inden-1-one;

[0085] Weigh raw material A, raw material B, potassium persulfate, and HMPA in a molar ratio of 1:1.5:1:0.1, wherein (A) compound is 0.1 mmol. The reaction solution adopts DMSO, and the reaction system is o The reaction was stirred at C for 12 hours. Cool after the reaction, wash with saturated sodium chloride aqueous solution, remove water with anhydrous sodium sulfate, suction filter through a short silica gel column, rotary evaporate the filtrate, remove potassium persulfate, remove solvent, and use silica gel column chromatography for the residue, petroleum ether Rinse, TLC detection, combine the effluents containing the product, distill off the solvent with a rotary evaporator, and dry in vacuo to obtain the brown-yellow target product with a yield of 35% and a purity of 99...

specific example 2

[0086] Concrete example two: Synthesis of 3-(4-(methyl)benzene) using 3-(4-(methyl)benzene)-1-phenylprop-2-yn-1-ketone and silver trifluoromethanethiolate -2-((trifluoromethyl)thio)-1H-inden-1-one;

[0087] Weigh raw material A, raw material B, potassium persulfate, and HMPA at a molar ratio of 1:1.5:2:0.1, wherein (A) compound is 0.1 mmol. The reaction solution adopts DMSO, and the reaction system is o The reaction was stirred at C for 12 hours. Cool after the reaction, wash with saturated sodium chloride aqueous solution, remove water with anhydrous sodium sulfate, suction filter through a short silica gel column, rotary evaporate the filtrate, remove potassium persulfate, remove solvent, and use silica gel column chromatography for the residue, petroleum ether Rinse, TLC detection, combine the effluents containing the product, distill off the solvent with a rotary evaporator, and dry in vacuo to obtain the brown-yellow target product with a yield of 65% and a purity of 99...

specific example 3

[0088] Specific example three: Synthesis of 3-(4-(methyl)benzene) using 3-(4-(methyl)benzene)-1-phenylprop-2-yn-1-ketone and silver trifluoromethanethiolate -2-((trifluoromethyl)thio)-1H-inden-1-one;

[0089] Weigh raw material A, raw material B, potassium persulfate, and HMPA at a molar ratio of 1:1.5:3:0.1, wherein the compound (A) is 0.1 mmol. The reaction solution adopts DMSO, and the reaction system is o The reaction was stirred at C for 12 hours. Cool after the reaction, wash with saturated sodium chloride aqueous solution, remove water with anhydrous sodium sulfate, suction filter through a short silica gel column, rotary evaporate the filtrate, remove potassium persulfate, remove solvent, and use silica gel column chromatography for the residue, petroleum ether Rinse, TLC detection, combine the effluents containing the product, distill off the solvent with a rotary evaporator, and dry in vacuo to obtain the brown-yellow target product with a yield of 84% and a purity...

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Abstract

The invention discloses a preparation method of indanone with trifluoromethylthio group and its derivatives. In the method, acetylene compounds and silver trifluoromethanethiolate compounds are selected as raw materials, and a persulfate reagent is used as an oxidizing agent. Using hexamethylphosphoric triamide as a stabilizer, the reaction was carried out in a reaction solvent at a reaction temperature of 80 oC for 12 hours. After the reaction was completed, indanone compounds were obtained through post-processing. This preparation method solved the problem of solving the problem of amides It is a technical problem to directly generate indanones by combining heterocyclic rings, and the preparation method has many advantages such as economical and cost-effective, high stability, mild reaction conditions, short reaction time, cheap and easy-to-obtain raw materials, and high product yield and purity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to an indanone with a trifluoromethylthio group, its derivatives and a preparation method thereof. Background technique [0002] Trifluoromethylthio (-SCF3) has strong electron-withdrawing effect, high lipophilicity (hydrophobic parameter ) and good biological activity, so introducing it into organic compounds can significantly change the chemical stability and metabolic stability of the compound. Therefore, containing -SCF 3 Based compounds have great potential application value in the fields of medicine, agrochemicals and materials. For example, the anti-coccidial drug Toltrazuril (Toltrazuril), the insecticide (Vaniliprole), the anorexia drug Tiflorex (Tiflorex), the antihypertensive drug Losartan (Losartan analogue), etc., all contain trifluoro Methylthio, as shown in the following chemical structural formula: [0003] [0004] Based on the excellent properties...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/22
CPCC07C319/14C07C323/22
Inventor 钱鹏程
Owner 瑞安宝源化工有限公司
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