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Trifluoromethylthiolation reagent and application thereof

A technology of trifluoromethylthio and sodium trifluoromethylsulfinate, applied in the direction of organic chemistry, etc., can solve the problems of high toxicity, difficulty in preparation and expensive raw materials of trifluoromethylthio flower reagent, and achieve high yield , Substrate adaptability, cheap effect

Inactive Publication Date: 2017-05-31
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The above types of trifluoromethylthio flower reagents have the disadvantages of high toxicity, instability, or difficulty in preparation, and expensive raw materials.

Method used

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  • Trifluoromethylthiolation reagent and application thereof
  • Trifluoromethylthiolation reagent and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] In a reactor containing solvent toluene, add sodium trifluoromethylsulfinate (62.4g), indole (23.4g), dimethyl phosphite (55mL), iodine element (about 10g) and copper acetate (50g ), stirred at 110° C. for more than 12 hours under nitrogen protection conditions. After the reaction, the product 3-trifluoromethylthioindole was obtained after filtration, distillation and column chromatography separation. , the yield was 89%.

Embodiment 2

[0023] In a reactor containing solvent toluene, add sodium trifluoromethanesulfinate (62.4g), indole (23.4g), diethyl phosphite (60mL), iodine element (about 10g) and copper acetate (50g ), stirred at 110° C. for more than 12 hours under nitrogen protection conditions. After the reaction, the product 3-trifluoromethylthioindole was obtained after filtration, distillation and column chromatography separation. , and the yield was 87%.

Embodiment 3

[0025] In the reactor containing solvent toluene, add sodium trifluoromethyl sulfinate (62.4g), N-methylindole (26.2g), diethyl phosphite (60mL), iodine simple substance (about 10g) and Copper acetate (50 g), stirred at 110° C. under nitrogen protection for more than 12 hours. After the reaction, the product N-methyl-3-trifluoromethylthioindole was obtained after filtration, distillation and column chromatography separation. , and the yield was 84%.

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Abstract

The invention discloses a trifluoromethylthiolation reagent and the application of the trifluoromethylthiolation reagent. The application of the trifluoromethylthiolation reagent comprises the following steps: adding sodium trifluoromethanesulfinate, indole and derivatives of the indole, appropriate amounts of dimethyl phosphate, iodine elements and copper acetate in a reactor containing a toluene solvent, stirring for 12h under the protection of nitrogen at the temperature of 110 DEG C; filtering reaction produced liquid, and distilling off low-boiling point substances; performing ethyl acetate / petroleum ether column chromatography isolation to obtain the product, 3-trifluomethylthio indole. The trifluoromethylthiolation reagent, namely sodium trifluoromethanesulfinate which is low in cost and readily available, is used, so that the synthesizing cost is greatly reduced and the process is simple to operate.

Description

technical field [0001] The invention relates to a trifluoromethylthiolation reagent and application thereof, belonging to the field of organic chemistry. Background technique [0002] In the past two years, there have been more papers on direct trifluoromethylthiolation than in the past. It is well known that trifluoromethylthio (SCF3) has strong electron-withdrawing properties and high lipophilicity (πR=1.44), and the enhancement of lipophilicity is conducive to improving the penetration and absorption rate of organic molecules, so trifluoromethylsulfide compounds in The field of medicine, pesticide and materials has great application prospects, and it also has important application value in organic synthesis. At present, molecules containing trifluoromethylthio with important biological activities mainly include the anticoccidial drug Toltrazuril, the anorexia drug Tiflorex, and the antihypertensive drug Losartan (Losartan analogue) Wait. [0003] From the development h...

Claims

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Application Information

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IPC IPC(8): C07C313/02C07D209/30
CPCC07C313/02C07D209/30
Inventor 蒋绿齐易文斌
Owner NANJING UNIV OF SCI & TECH
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