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A kind of method of synthesizing aromatic acetamide

An aromatic acetamide and compound technology, which is used in the fields of pesticides, organic chemicals, and medicine to avoid the use of alkylating reagents, reduce amide synthesis steps, and save costs.

Active Publication Date: 2022-05-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the traditional synthetic method, a large number of toxic alkyl halides are used as alkylating reagents in the presence of stoichiometric inorganic bases, and multi-step reactions are required, resulting in a large number of harmful by-products

Method used

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  • A kind of method of synthesizing aromatic acetamide
  • A kind of method of synthesizing aromatic acetamide
  • A kind of method of synthesizing aromatic acetamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of 2,3-diphenylpropanamide

[0027]

[0028] Benzyl alcohol (0.216 g, 2.0 mmol) and phenylacetonitrile (0.117 g, 1.0 mmol) were dissolved in 1.0 mL of tert-amyl alcohol and mixed with 7.9 mg (1.0 mol%) of [Cp*IrCl 2 ] 2 , 3.6 mg (2.0 mol %) of 1,10-phenanthroline, and 22.4 mg (20 mol %) of potassium tert-butoxide were added to a pressure-resistant tube, and after nitrogen replacement, the reaction was carried out at 140° C. for 6 h. The obtained reaction solution was cooled to room temperature, extracted with water and ethyl acetate, the organic phase was separated, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by rapid preparative liquid chromatography (volume ratio of ethyl acetate: petroleum ether was 30:100). The eluate containing the target compound was collected, and 0.203 g of the compound represented by formula 3 was obtained by rotary evaporation under reduced pressure, with a yield of 90% and a liquid pha...

Embodiment 2

[0029] Example 2: Synthesis of 2,3-diphenylpropanamide

[0030] Benzyl alcohol (0.108 g, 2.0 mmol) and phenylacetonitrile (0.117 g, 1.0 mmol) were dissolved in 0.5 mL of tetrahydrofuran and mixed with 1.4 mg (0.2 mol%) of [Ir(cod)Cl 2 ] 2 , 1.1 mg (0.4 mol %) of triphenylphosphine and 22.4 mg (20 mol %) of potassium tert-butoxide were added together into a pressure-resistant tube, and after nitrogen replacement, the reaction was carried out at 160° C. for 10 h. The obtained reaction solution was cooled to room temperature, extracted with water and ethyl acetate, the organic phase was separated, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by rapid preparative liquid chromatography (volume ratio of ethyl acetate: petroleum ether was 30:100). The eluate containing the target compound was collected, and 0.101 g of the compound represented by formula 3 was obtained by rotary evaporation under reduced pressure, with a yield of 45% and a liquid phase...

Embodiment 3

[0031] Example 3: Synthesis of 2,3-diphenylpropanamide

[0032] Benzyl alcohol (0.540 g, 2.0 mmol) and phenylacetonitrile (0.117 g, 1.0 mmol) were dissolved in 5.0 mL of dioxane and mixed with 14.4 mg (5 mol%) of IrCl 3 , 62.2 mg (10.0 mol%) of (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and 28 mg (50 mol%) of potassium hydroxide were added to the pressure-resistant tube After nitrogen replacement, the reaction was carried out at 80 °C for 2 h. The resulting reaction solution was cooled to room temperature, extracted with water and ethyl acetate, the organic phase was separated, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by rapid preparative liquid chromatography (the volume ratio of ethyl acetate: petroleum ether was 30:100). The eluate containing the target compound was collected, and 0.027 g of the compound represented by formula 3 was obtained by rotary evaporation under reduced pressure, with a yield of 12% and a liquid phase purity...

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Abstract

In the present invention, compound 1 and compound 2 are dissolved in an organic solvent, catalysts, ligands and basic substances are added, reacted at 80°C to 160°C for 2h to 10h under a protective atmosphere, and the resulting reaction solution is post-treated to obtain compound 3. The present invention utilizes alcohol and aryl acetonitrile to synthesize aryl acetoamide in one step, which not only avoids the use of toxic alkylating reagents, but also reduces amide synthesis steps and saves costs; no by-products are produced in the reaction process, and the atoms can be utilized The rate reached 100%, in line with the development requirements of green chemistry.

Description

(1) Technical field [0001] The invention relates to a completely atom-economical method for directly synthesizing aromatic acetamide compounds from alcohol and aromatic acetonitrile, and relates to the fields of medicine, pesticide and organic chemical industry. (2) Background technology [0002] Amides are ubiquitous in a variety of biologically active natural products, drugs, and pharmaceuticals, and they have the potential to be transformed into versatile building blocks for the construction of carboxylic acids, ketones, heterocycles, and oxazolines. Therefore, it is very important to develop a new strategy for the production of amide compounds. In particular, the construction of carbon-carbon bonds is an important route for the synthesis of amides. In traditional synthetic methods, a large amount of toxic alkyl halides are used as alkylating reagents in the presence of stoichiometric amounts of inorganic bases, and multi-step reactions are required, resulting in a large...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/06C07C233/11C07C235/34C07C233/13C07D213/56C07D333/38
CPCC07C231/06C07D213/56C07D333/38C07C2601/02C07C2602/26C07C233/11C07C235/34C07C233/13
Inventor 许丹倩李晨夏爱宝
Owner ZHEJIANG UNIV OF TECH
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