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N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application

A technology of tosyl trifluoroacetamide and trifluoroacetophenone is applied in the field of pharmaceutical chemical intermediates and related chemistry, can solve the problems of low atom economy, chemical waste and the like, achieves environmental friendliness, low reaction cost, high yield effect

Active Publication Date: 2019-07-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these reaction types have unavoidable limitations, requiring specific reaction substrates, low atom economy, and unutilized by-products brought by trifluoroacetylating reagents during the reaction, resulting in chemical waste.

Method used

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  • N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application
  • N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application
  • N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Synthesis of 2,2,2-trifluoro-1-((1,1'-biphenyl-4-yl)ethanone

[0041] In a 25mL reactor, add palladium acetate (0.0023g, 0.01mmol), potassium carbonate (0.0553g, 0.4mmol), tri-tert-butylphosphine (0.0041g, 0.02mmol) and NTFTS (0.0687g, 0.2mmol), nitrogen After three replacements, 2 mL of anhydrous toluene was added, 4-biphenylboronic acid (0.0792 g, 0.4 mmol) was added with stirring, and stirred at 25°C for 24 h. Column chromatography (silica gel, 200-300 mesh; developer, petroleum ether: ethyl acetate = 100:1) to obtain 2,2,2-trifluoro-1-((1,1'-biphenyl-4-yl ) ethyl ketone 0.0491g, productive rate 98%.

[0042] 2,2,2-Trifluoro-1-((1,1'-biphenyl-4-yl)ethanone

[0043] white solid, 1 H NMR (500MHz, CDCl 3 )δ8.16(d, J=8.5Hz, 2H), 7.77(d, J=8.5 Hz, 2H), 7.65(d, J=8.0Hz, 2H), 7.52-7.49(m, 2H), 7.46- 7.44(m,1H); 13 C NMR (126MHz, CDCl 3 )δ180.24(q, J=35.0Hz), 148.37, 139.27, 130.89(q, J=1.8Hz), 129.27, 129.05, 128.72, 127.79, 127.51, 116.91(q, J=291.3Hz) ...

Embodiment 2

[0044] Example 2: Synthesis of 2,2,2-trifluoro-1-(3-tolyl)ethanone

[0045] The operation was the same as in Example 1, and 0.0252 g of 2,2,2-trifluoro-1-(3-methylphenyl)ethanone was obtained by reacting 3-methylphenylboronic acid with NTFTS, with a yield of 67%.

[0046] 2,2,2-Trifluoro-1-(3-methylphenyl)ethanone

[0047] colorless liquid, 1 H NMR (500MHz, CDCl 3 )δ7.88-7.87(m,2H),7.52(d,J=7.6Hz,1H),7.45-7.42(m,1H),2.45(s,3H); 13 C NMR (125MHz, CDCl 3 )δ180.80(q, J=34.8Hz), 139.25, 136.50, 130.61(q, J=1.8Hz), 130.09, 129.08, 127.52(q, J=2.1 Hz), 116.85(q, J=291.4Hz) ,21.45

Embodiment 3

[0048] Example 3: Synthesis of 2,2,2-trifluoro-1-((4-tert-butyl)phenyl)ethanone

[0049] In a 25mL reactor, tris(dibenzylideneacetone)dipalladium (0.0046g, 0.005mmol), tricyclohexylphosphine (0.0057g, 0.02mmol) and NTFTS (0.0687g, 0.2mmol), nitrogen replacement 3 times , 2 mL of anhydrous 1,4-dioxane was added, 4-tert-butylphenylboronic acid (0.0534 g, 0.3 mmol) was added with stirring, and stirred at 30° C. for 24 h. Column chromatography (silica gel, 200-300 mesh; developer, petroleum ether: ethyl acetate = 100:1) to obtain 2,2,2-trifluoro-1-((4-tert-butyl)phenyl)ethanone 0.0276g, 60% yield.

[0050] 2,2,2-Trifluoro-1-((4-tert-butyl)phenyl)ethanone

[0051] white solid, 1 H NMR (500MHz, CDCl 3 )δ8.02(d, J=7.9Hz, 2H), 7.56(d, J=8.6 Hz, 2H), 1.36(s, 9H); 13 C NMR (125MHz, CDCl 3 )δ180.24(q, J=34.8Hz), 159.97, 130.31(q, J=2.1Hz), 127.48, 126.27, 116.92(q, J=291.5Hz), 35.61, 31.04

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Abstract

The invention belongs to the technical field of medical chemical engineering intermediates and related chemistry, and relates to N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application. The N-phenyl-N-p-toluenesulfonyl trifluoroacetamide is taken as a trifluoroacetylation reagent, reacts with an arylboronic acid derivative in an anhydrous organic solvent under the action of a metalcatalyst, a ligand and an alkali, and is efficiently and highly selectively converted into a trifluoroacetophenone compound. According to a synthesis method of the trifluoroacetophenone compound, involved in the invention, reaction steps are few; the NTFTS which is stable in use, easy to store, cheap and easy to get is taken as a trifluoroacetyl source; environmental friendliness is realized; reaction conditions are mild; operation is easy; a high-yield and high-selectivity target product is obtained and has relatively good industrial production value and practical application value. The trifluoroacetophenone compound synthesized by utilizing the method can be further subjected to a functionalization reaction, and can be widely applied to the synthetic fields of medicine, pesticide, bioactive molecules, functional material molecules and the like.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a kind of N-phenyl-N-p-toluenesulfonyl trifluoroacetamide and the preparation of trifluoroacetophenone compound using novel trifluoroacetylation reagents method. Background technique [0002] Trifluoroacetophenone compound is an important intermediate in organic synthesis. The characteristics of high electronegativity and small atomic radius of fluorine atom can improve the metabolic stability and fat solubility of trifluoroacetophenone compound, making it widely used in synthetic medicine , pesticides, natural products, bioactive molecules, organic functional materials and other important fields. It is of great practical significance and application value to prepare a new type of trifluoroacetylation reagent for the efficient and selective synthesis of trifluoroacetophenone compounds. [0003] The development of synthetic...

Claims

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Application Information

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IPC IPC(8): C07C311/51C07C45/45C07C49/813C07C49/80C07C49/84C07C67/313C07C69/76
CPCC07C45/455C07C67/313C07C311/51C07C49/813C07C49/80C07C49/84C07C69/76
Inventor 包明李文宽唐荧王万辉张胜
Owner DALIAN UNIV OF TECH
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