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Preparation method of aniline para-trifluoromethylated derivative

A technology for trifluoromethylation and aniline derivatives is applied in the field of preparation of para-trifluoromethylated derivatives of aniline, and can solve the problems of low yield of stoichiometric metal salts, expensive reagents, narrow substrate range, and the like, To achieve the effect of easy availability of raw materials, simple post-processing process and various types

Active Publication Date: 2021-08-06
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The shortcoming of above-mentioned formula (1) is that substrate scope is narrow, and stoichiometric metal salt yield is low, and above-mentioned formula (2) shortcoming is no regioselectivity, and substrate scope is narrow, and reagent is expensive

Method used

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  • Preparation method of aniline para-trifluoromethylated derivative
  • Preparation method of aniline para-trifluoromethylated derivative
  • Preparation method of aniline para-trifluoromethylated derivative

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preparation example Construction

[0026] The invention provides a preparation method of para-trifluoromethylated aniline derivatives, which comprises: sequentially adding aniline derivatives, 4,5-dichlorofluorescein, potassium persulfate, trifluoromethyl Put sodium sulfonate into a stirrer, use dimethyl sulfoxide as a solvent, and stir at 500 rpm for 11 hours at 23-25°C under 40W blue LED irradiation. After the reaction is completed, the product is subjected to column chromatography separation and purification treatment to obtain the para-trifluoromethylated aniline derivative.

[0027] The reaction process of above-mentioned technical scheme can be expressed as:

[0028]

Embodiment 1

[0032] This implementation case shows a preparation method of aniline para-trifluoromethylated derivatives according to the following steps: using N-Boc aniline as a raw material, the reaction formula is as follows:

[0033]

[0034] (1) Add 0.0386 grams (0.2 mmol) of N-Boc aniline, 0.0016 grams (4 mmol%) of 4,5-dichlorofluorescein, 0.1621 grams (0.6 mmol) of potassium persulfate, trifluoroform 0.0624 g (0.4 mmol) of sodium sulfinate and 2 ml of dimethyl sulfoxide were screwed on and placed between two 40w blue LEDs, and stirred at room temperature (23-25° C.) for 11 hours.

[0035] (2) Add water to quench the reaction after the reaction is completed, extract three times with ethyl acetate, combine the organic layers, and dry the solution with anhydrous sodium sulfate, spin the solvent under reduced pressure and separate by column chromatography (petroleum ether: ethyl acetate = 10:1) gave the product (73% yield).

[0036] 1 H NMR (400MHz, Chloroform-d) δ7.52(d, J=7.7Hz, ...

Embodiment 2

[0038] This implementation case shows a preparation method of aniline para-trifluoromethylated derivatives according to the following steps: using 2-ethyl-N-Boc aniline as a raw material, the reaction formula is as follows:

[0039]

[0040] (1) Add 0.0442 grams (0.2 mmol) of 2-ethyl-N-Boc aniline, 0.0016 grams (4 mmol%) of 4,5-dichlorofluorescein, and 0.1621 grams (0.6 mmol %) of potassium persulfate to a colorless glass bottle successively. ), 0.0624 g (0.4 mmol) of sodium trifluoromethanesulfinate and 2 ml of dimethyl sulfoxide, screw the lid on and place between two 40w blue LEDs, stir at room temperature (23-25°C) for 11 Hours.

[0041] (2) Add water to quench the reaction after the reaction is completed, extract three times with ethyl acetate, combine the organic layers, and dry the solution with anhydrous sodium sulfate, spin the solvent under reduced pressure and separate by column chromatography (petroleum ether: ethyl acetate = 10:1) gave the product (67% yield)....

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Abstract

The invention discloses a preparation method of an aniline para-trifluoromethylated derivative. The method comprises the following steps: sequentially adding an aniline derivative, 4, 5-dichlorofluorescein, potassium persulfate and sodium trifluoromethanesulfinate into a glass reaction tube, and reacting at room temperature (23-25 DEG C) under 40W blue LED (light-emitting diode) by taking dimethyl sulfoxide as a solvent to obtain the aniline para-trifluoromethylated derivative. According to the invention, the aniline derivative is used as an initiator, and the raw materials are easily available and various; products obtained by the method disclosed by the invention have various types and can be directly applied to modification of drug molecules; and meanwhile, the synthesis route is safe and easy to implement, the cost is low, the reaction operation and post-treatment process are simple, the selectivity is good, the side reaction is few, and the amplification reaction can be carried out.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis and relates to a preparation method of para-trifluoromethylated aniline derivatives. Background technique [0002] The para-trifluoromethylated derivatives of aniline have significant biological activity and pharmacological activity, such as: leflunomide is a selective immunosuppressant, which can inhibit the immune response of the body and inhibit T cells related to immune response The proliferation and function of macrophages such as B cells and B cells can reduce the immune response of antibodies. It is clinically used in the treatment of adult rheumatoid arthritis, which can prevent the destruction of joint bone, control the further development of the disease, and protect the function of joint muscles. , to delay the occurrence of joint deformities and the loss of joint function; another example: teriflunomide is a new drug for the treatment of relapsing multiple sclerosis. In the fi...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C271/28C07C253/30C07C255/19C07C231/12C07C233/15C07D263/58
CPCC07C269/06C07C253/30C07C231/12C07D263/58C07C271/28C07C255/19C07C233/15Y02P20/55
Inventor 赵应声蒋雅琦琪史达清
Owner SUZHOU UNIV
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