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Alpha-thioether aryl acetonitrile compound and synthesis method thereof

An arylacetonitrile and compound technology, applied in the field of α-thioether arylacetonitrile compounds and their synthesis, can solve the problems of harsh reaction conditions, expensive raw material preparation, limited product types, etc., and achieves easy availability of raw materials and good application prospects , mild conditions

Active Publication Date: 2019-09-17
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the types of synthesized products are relatively limited; some substrates are relatively complex and often need to be obtained through several steps of reaction, and the preparation of raw materials is relatively expensive; or the reaction conditions are relatively harsh, complicated, difficult to popularize, and the reaction cost is high

Method used

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  • Alpha-thioether aryl acetonitrile compound and synthesis method thereof
  • Alpha-thioether aryl acetonitrile compound and synthesis method thereof
  • Alpha-thioether aryl acetonitrile compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: 2-(tert-butylthio)-2-phenylacetonitrile

[0041] 2-(tert-butylthio)-2-phenylacetonitrile adopts the following steps: 1. add 5.4 grams of benzyl sulfide (30 mmol) in a 500 milliliter three-necked flask, 6.1 milliliters of tert-butylisonitrile (54 mmol), 0.78 grams of three Silver fluoromethanesulfonate (3 mmol), 13.60 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (60 mmol), 300 ml of toluene, heated to 100°C. Track the reaction with thin-layer chromatography, and react until the raw materials disappear after 3 hours; ② The crude product obtained after removing the solvent from the reaction system is directly separated and purified by column chromatography (developing solvent: petroleum ether: ethyl acetate=100:1), Obtain 4.3 grams of 2-(tert-butylthio)-2-phenylacetonitrile, whose structural formula is: The yield was 70%. This compound belongs to the first reported synthesis, and the synthesis method has mild reaction conditions, good yield and good applica...

Embodiment 2

[0047] Example 2: 2-[(1,1'-biphenyl)-4-yl]-2-(tert-butylthio)acetonitrile

[0048] 2-[(1,1'-biphenyl)-4-yl]-2-(tert-butylthio)acetonitrile adopts the following steps: 1. Add 7.69 grams of ([1,1'- Biphenyl]-4-ylmethyl)(tert-butyl)sulfide (30mmol), 6.8ml tert-butylisonitrile (60mmol), 1.17g silver triflate (4.5mmol), 27.20g 2,3-bis Chloro-5,6-dicyano-1,4-benzoquinone (120mmol), 300ml of toluene, heated to 100°C. Track the reaction with thin-layer chromatography, and react until the raw materials disappear after 3 hours; ② The crude product obtained after removing the solvent from the reaction system is directly separated and purified by column chromatography (developing solvent: petroleum ether: ethyl acetate=100:1), Obtain 2.83 grams of 2-[(1,1'-biphenyl)-4-yl]-2-(tert-butylthio)acetonitrile, whose structural formula is: The yield was 34%. This compound belongs to the first reported synthesis, and the synthesis method has mild reaction conditions, good yield and good applic...

Embodiment 3

[0055] Example three: 2-(tert-butylthio)-2-(4-isopropylphenyl)acetonitrile

[0056] 2-(tert-butylthio)-2-(4-isopropylphenyl) acetonitrile adopts the following steps: 1. add 6.67 grams of tert-butyl (4-isopropylbenzyl) sulfide in a 500 ml three-necked flask Ether (30 mmol), 6.1 mL tert-butylisonitrile (54 mmol), 0.78 g silver triflate (3 mmol), 13.60 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone ( 60mmol), 300ml of toluene, heated to 100°C. Track the reaction with thin-layer chromatography, and react until the raw materials disappear after 3 hours; ② The crude product obtained after removing the solvent from the reaction system is directly separated and purified by column chromatography (developing solvent: petroleum ether: ethyl acetate=100:1), Obtain 4.59 grams of 2-(tert-butylthio)-2-(4-isopropylphenyl)acetonitrile, whose structural formula is: The yield was 62%. This compound belongs to the first reported synthesis, and the synthesis method has mild reaction conditions, g...

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Abstract

The invention relates to a synthesis method of an alpha-thioether aryl acetonitrile compound. A structural formula of the compound is as shown in the specification, wherein R1 = hydrogen, methyl, isopropyl, phenyl, fluorine or bromine; R2 = hydrogen, methyl or chlorine; R3 = hydrogen, methyl or bromine; and R4 = tert-butyl or 1-adamantyl. According to the method, raw materials are simple and easy to obtain, t-butyl isocyanide is used as a cyano source of a reaction, and relatively high reactivity is exhibited under catalysis of silver trifluoromethanesulfonate. In a reaction process, the operation is simple, the condition is mild, the environment is friendly, and the yield is general to moderate. New compounds can be synthesized by applying the method, and the new compounds have potential medicinal values, so that the method has good application prospects in industrial production.

Description

technical field [0001] The invention relates to an α-sulfide aryl acetonitrile compound and a synthesis method thereof. Background technique [0002] Nitrile compounds are common compounds in organic synthesis and have been widely used in the preparation of carboxylic acids, amides, aldehydes, ketones, amidines, amines and other compounds, and as important precursors for the construction of nitrogen-containing heterocycles with important physiological functions. For example, in 2008, Saito et al. used a rhodium catalyst system to form amides through hydration of organic nitriles under mild conditions, see: Saito, S.etal.Angew.Chem., Int.Ed.2008,47,3607 ; In 2015, Perry et al. developed a novel chromogenic reagent to screen the activity of nitrilase, which can be used as a substitute for Nessler's reagent (Nessler's reagent) to promote the hydrolysis of nitrile, see: Perry, J .et al.Chem.Commun.2015,51,2660; In the same year, Milstein et al. first converted nitriles to prima...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/56
CPCC07C323/56C07C2603/74
Inventor 许斌邹闽芬刘秉新谭启涛王辉丁昌华
Owner SHANGHAI UNIV
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