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Synthesis method of sulfur-containing gamma, gamma-bis-arylamine butyramide compound

A technology of bisarylamine butanamide and synthesis method, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of sulfides, etc., can solve problems such as palladium catalyst poisoning, rare reports, etc. Simple, protect the health of environmental operators

Active Publication Date: 2021-12-31
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Probably because sulfur atoms easily poison the palladium catalyst ( Org. Lett . 2012, 14 , 2164-2167), so far, N , S - Bidentate-oriented difunctionalization of alkenes is rarely reported

Method used

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  • Synthesis method of sulfur-containing gamma, gamma-bis-arylamine butyramide compound
  • Synthesis method of sulfur-containing gamma, gamma-bis-arylamine butyramide compound
  • Synthesis method of sulfur-containing gamma, gamma-bis-arylamine butyramide compound

Examples

Experimental program
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specific Embodiment 1

[0018] Specific embodiment one: 44.2 milligrams (0.2 mmol) N-(2-(ethylthio) phenyl) but-3-enamide, 62.06 milligrams (0.58 mmol) N-methylaniline, 4.5 milligrams (0.02 mmol) ) palladium acetate as catalyst, 3.2 mg (0.02 mmol) ferric chloride and 10.4 mg (0.06 mmol) ferrous acetate as oxidant, 29.3 mg (0.24 mmol) benzoic acid as additive, in 3 ml solvent acetonitrile, at 90 o C stirred the reaction for 24 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, and use a rotary evaporator to remove the solvent to obtain the residue, and the residue is leached through a silica gel column with an eluent prepared with petroleum ether and ethyl acetate at a volume ratio of 3:1. Wash, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, use a rotary evaporator to remove the solvent from the combined effluent, and dry in vacuo to obtain a buttery N-(2-(ethylthio) Phenyl)-4,4-bis(4-(methyla...

specific Embodiment 2

[0019] Specific embodiment two: 44.2 mg (0.2 mmol) N-(2-(ethylthio) phenyl) but-3-enamide, 70.18 mg (0.58 mmol) N-ethylaniline, 4.5 mg (0.02 mmol) ) palladium acetate as catalyst, 3.2 mg (0.02 mmol) ferric chloride and 10.4 mg (0.06 mmol) ferrous acetate as oxidant, 29.3 mg (0.24 mmol) benzoic acid as additive, in 3 ml solvent acetonitrile, at 90 o C stirred the reaction for 24 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, and use a rotary evaporator to remove the solvent to obtain the residue, and the residue is leached through a silica gel column with an eluent prepared with petroleum ether and ethyl acetate at a volume ratio of 3:1. Wash, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, use a rotary evaporator to remove the solvent from the combined effluent, and dry in vacuo to obtain buttery 4,4-bis(4-(B (amino)phenyl)-N-(2-(ethylthio)phenyl)butanamide 52.7 mg,...

specific Embodiment 3

[0020] Specific example three: 44.2 mg (0.2 mmol) N-(2-(ethylthio) phenyl) but-3-enamide, 78.30 mg (0.58 mmol) cumylaniline, 4.5 mg (0.02 mmol) Palladium acetate was used as catalyst, 3.2 mg (0.02 mmol) ferric chloride and 10.4 mg (0.06 mmol) ferrous acetate were used as oxidant, 29.3 mg (0.24 mmol) benzoic acid was used as additive, in 3 ml solvent acetonitrile, at 90 o C stirred the reaction for 24 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, and use a rotary evaporator to remove the solvent to obtain the residue, and the residue is leached through a silica gel column with an eluent prepared with petroleum ether and ethyl acetate at a volume ratio of 3:1. Wash, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, use a rotary evaporator to remove the solvent from the combined effluent, and dry in vacuo to obtain buttery N-(2-(ethylthio )phenyl)-4,4-bis(4-(isopropylam...

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Abstract

The invention relates to a method for synthesizing a sulfur-containing gamma, gamma-bis-arylamine butyramide compound, which comprises the following steps of: stirring N-(2-(ethylthio)phenyl)butyl-3-acrylamide serving as a reaction substrate, arylamine serving as a nucleophilic reagent, palladium acetate serving as a catalyst, ferric trichloride and ferrous acetate serving as oxidants, benzoic acid serving as an additive and acetonitrile serving as a solvent, at 90 DEG C to react for 24 hours; and after the reaction is finished, filtering the reaction liquid, removing the solvent from the filtrate by using a rotary evaporator to obtain a residue, carrying out column chromatography separation on the residue by using a silica gel column, leaching the residue by using an eluent, collecting effluent containing a target product, combining the effluent, and carrying out vacuum concentration to remove the solvent to obtain the target product. The method has the advantages of simple and easily available raw materials, relatively mild reaction conditions, novel and simple preparation process, less pollution and low energy consumption.

Description

technical field [0001] The invention relates to a method for synthesizing sulfur-containing γ, γ-bisarylamine butanamide compounds. Background technique [0002] Olefins are the most abundant class of organic molecules and are available in large quantities from petrochemical feedstocks and renewable resources. The ubiquity of alkenes and their unique reactivity have made alkenes functionalization a common reaction in organic synthesis, and transition metal-catalyzed difunctionalization of alkenes has been developed as an important strategy for rapid access to a variety of valuable Structural units found in the building blocks of pharmaceuticals and natural products. In recent years, a number of research groups at home and abroad have completed a series of excellent work in this field. In 2016, Engle research group reported palladium (II) catalyzed unactivated alkenes β, γ-bifunctionalization reaction ( J. Am. Chem. Soc . 2016, 138 , 15122-15125); in 2018, Engle's group r...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C319/28C07C323/41
CPCC07C319/20C07C319/28C07C323/41Y02P20/584
Inventor 张兴国杨松张小红康田梦
Owner WENZHOU UNIVERSITY
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