Aryl amide derivative containing tertiary carbon center and preparation method thereof

Abstract

The invention provides an aryl amide derivative containing a tertiary carbon center and a preparation method thereof. The preparation method comprises the following steps: in an inert atmosphere, adding aryl amide, a metal reducing agent, an iron catalyst and secondary chloralkane into an organic solvent, stirring at normal temperature for reaction, and quenching, separating and purifying after the reaction is completed to obtain the aryl amide derivative with the para-position being the tertiary carbon center. The method has the advantages of simple operation, easily available raw materials, mild reaction conditions and considerable yield.

Description

Technical Field

[0001] The invention belongs to the technical field of synthesis of aryl amide compounds, and in particular relates to an aryl amide derivative containing a tertiary carbon center and a preparation method thereof. Background Art

[0002] Arylamides are a common class of organic compounds that are widely found in various common chemicals, pharmaceuticals, and complex natural products (e.g. Figure 1 Therefore, it is of great research value to explore an economical, environmentally friendly and highly selective method for achieving para-functionalization of aromatic amides.

[0003] According to the development requirements of atom economy and step economy advocated by green chemistry, directly functionalizing inert CH bonds can avoid the pre-functionalization step and effectively shorten the transformation process. In organic synthetic chemistry, transition metal-catalyzed direct functionalization of CH bonds has become the focus of chemists due to its significant advantages such as high efficiency, atom economy and environmental friendliness.

[0004] In the past decade, highly regioselective CH bond functionalization reactions have achieved phased research results. Usually, regioselective CH bond functionalization uses directing groups to form stable cyclometallated intermediates to achieve ortho, meta or para CH bond functionalization reactions. However, compared with the ortho and meta CH bond functionalization reactions assisted by directing groups, para CH bond functionalization reactions face huge challenges. When adopting the directing strategy, it is difficult to form a stable cyclometallated intermediate because the metal coordination center is the farthest from the para position; at the same time, the electron cloud density of the para CH bond is relatively low, which makes its interaction with the catalyst or reaction reagent weak, and it is difficult to form a stable transition state. These factors together lead to the difficulties in the para CH bond functionalization of aromatic amides.

[0005] Therefore, it is urgent to explore a method that can successfully functionalize the para-CH bond of aromatic amides. Summary of the invention

[0006] The purpose of the present invention is to provide an aromatic amide derivative containing a tertiary carbon center and a preparation method thereof. The method is a method for cleaving the para-carbon-hydrogen bond of the aromatic amide catalyzed by iron and reacting with a secondary chloroalkane to construct a tertiary carbon center, and is a preparation method for the aromatic amide derivative of the secondary carbon.

[0007] To achieve the above purpose, the technical solution provided by the present invention is:

[0008] An aromatic amide derivative containing a tertiary carbon center and a preparation method thereof, wherein:

[0009] Under an inert atmosphere, an arylamide, a metal reducing agent (active metal element), an iron catalyst, and a secondary chloroalkane are added to an organic solvent, and the reaction is carried out with stirring at room temperature. After the reaction is completed, it is quenched, separated and purified to obtain an arylamide derivative with a tertiary carbon center at the para position;

[0010] The general synthesis formula is as follows:

[0011]

[0012] Among them, R 3 Cl is a secondary chloroalkane; R 1 , R 2 are both aliphatic or aromatic groups.

[0013] Furthermore, the molar ratio of the arylamide, the secondary chloroalkane, and the metal reducing agent is 1∶2 - 4∶1 - 2.5, preferably 1∶4∶2.5;

[0014] The dosage ratio of the organic solvent to the arylamide is 2.5∶1 (mL∶mmol), that is, 2.5 mL of the organic solvent is required for each millimole of the arylamide;

[0015] The dosage of the iron catalyst is 5 - 10% of the amount of substance of the arylamide, preferably 10%.

[0016] Furthermore, the reaction time is 24 - 48 h; thin-layer chromatography is used for tracking during the reaction; for a more complete reaction, 48 h is preferred.

[0017] Furthermore, the secondary chloroalkane is isopropyl chloride or 2-chlorohexane;

[0018] The metal reducing agent is aluminum, manganese, indium, magnesium or zinc; magnesium is preferably used as the metal reducing agent.

[0019] The iron catalyst is ferric chloride, ferrous chloride, ferrous bromide, ferrous iodide, iron trifluoromethanesulfonate or iron acetylacetonate; ferrous iodide is preferably used as the iron catalyst.

[0020] The organic solvent is tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentyl methyl ether, cyclohexane, n-hexane or 1,4-dioxane, and tetrahydrofuran is preferably used as the reaction solvent.

[0021] Furthermore, the specific operation of separation and purification is to first extract with ethyl acetate, then dry with anhydrous Na2SO4, filter, reduce the pressure, and finally purify by column chromatography to obtain the arylamide derivative.

[0022] Furthermore, when the arylamide is a compound of formula I and the secondary chloroalkane is isopropyl chloride, the product is a compound of formula I'.

[0023]

[0024] Wherein, R1 is methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, p-methoxyphenyl or p-fluorophenyl.

[0025] Further, when the aromatic amide is a compound of formula II and the secondary chloroalkane is chloroisopropyl ethane, the product is a compound of formula II';

[0026]

[0027] Wherein, R2 is 3-methyl, 3-methoxy, 3-fluoro, 3-trifluoromethoxy, 3-dimethylamino, 3,5-dimethyl, 3,5-difluoro or 3-fluoro-5-methoxy.

[0028] Further, when the aromatic amide is N-1-naphthylbenzamide and the secondary halogenated alkane is a compound of formula III, the product is a compound of formula III';

[0029]

[0030] Wherein, R3 is isopropyl, isobutyl or isohexyl.

[0031] At the same time, the present invention provides an aromatic amide derivative containing a tertiary carbon center obtained by the above preparation method.

[0032] The advantages of the present invention are:

[0033] The present invention adopts a one-pot operation, is carried out at room temperature (mild conditions), uses aromatic amide and secondary chloroalkane as raw materials, uses active metal elements as reducing agents, and under the catalytic action of cheap metallic iron, successfully synthesizes aromatic amide derivatives with a tertiary carbon center at the para position, and has a considerable yield and low difficulty in separating and purifying the product; the method is a novel synthesis method for achieving high regional selectivity in constructing a tertiary carbon center.

[0034] The present invention uses iron as a catalyst, which has huge natural reserves and is relatively cheap in the market. Compared with rare metals or precious metals, it has significant cost advantages, and iron has the characteristics of low toxicity and good biocompatibility. However, although iron can be used as a catalyst for effectively catalyzing CH bond activation, research in the field of para-selective CH functionalization is still relatively scarce. Therefore, it is also very important to screen directing groups that are compatible with iron catalysts. The development of efficient iron-catalyzed para-CH bond activation of aromatic rings and the construction of CC bonds has important scientific significance and application value, both for the advancement of theoretical research and for the expansion of practical synthetic applications.

[0035] The development of the catalytic reaction system in the present invention provides a new method and new ideas for the study of iron-catalyzed arylamide alkylation reaction. The synthesis method has the advantages of easy access to raw materials, simple operation, mild reaction conditions, and considerable yield. It shows good prospects in practical applications and is expected to be widely used in related fields. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 It is a common aromatic amide derivative used in medicines or pesticides. DETAILED DESCRIPTION

[0037] The present invention is further described in detail below with reference to the accompanying drawings and specific embodiments:

[0038] The present invention uses an iron catalyst to realize the reaction of constructing the para-tertiary carbon center of aromatic amides, and specifically the synthesis method of aromatic amide derivatives containing tertiary carbon centers is as follows:

[0039] Under an inert atmosphere (such as argon), 5-10 mol% of an iron catalyst (such as ferric chloride, ferrous chloride, ferrous iodide, ferrous bromide, iron trifluoromethanesulfonate or ferric acetylacetonate), 0.4 mmol of an aromatic amide, 0.8 mmol-1.6 mmol of a secondary chloroalkane, 0.4 mmol-1.0 mmol of a metal reducing agent and 1 mL of a reaction solvent (such as tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentyl methyl ether, cyclohexane, n-hexane or 1,4-dioxane) are reacted at room temperature for 24-48 hours, and the reaction is tracked by TLC.

[0040] After the reaction is completed, the reactant is poured into 10-30 mL of aqueous ammonium chloride solution and extracted with 20-30 mL of ethyl acetate in portions, then dried over anhydrous Na2SO4, filtered, the solvent is removed under reduced pressure, and the target product is obtained by rapid silica gel column chromatography (ethyl acetate / petroleum ether=1:10-20).

[0041] Example 1

[0042]

[0043] 4-Isopropyl-N-(naphthalen-1-yl)benzamide

[0044] Under an argon atmosphere, N-1-naphthylbenzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours. The reaction was quenched by adding saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate, and the product was separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent, and the product was obtained with a yield of 92%.

[0045] The spectroscopic data of the obtained product are as follows:

[0046] 1 H NMR (500 MHz, CDCl3): δ = 8.25 (s, 1H), 8.01 (d, J = 7.4 Hz, 1H), 7.94–7.88 (m, 4H), 7.74 (d, J = 8.2 Hz, 1H), 7.54–7.49 (m, 3H), 7.37 (d, J = 8.2 Hz, 2H), 3.01 (dt, J = 13.8, 6.9 Hz, 1H), 1.31 (d, J = 6.9 Hz, 6H).

[0047] 13 C NMR (125 MHz, CDCl3): δ = 166.2, 153.2, 134.1, 132.5, 132.3, 128.7, 127.5, 127.3, 126.8, 126.3, 125.9, 125.7, 121.3, 120.8, 77.3, 77.0, 76.8, 34.1, 23.7.

[0048] HRMS (ESI + ): calcd for C 20 H 20 NO [M + H] + 290.15449, found 290.15436.

[0049] Example 2

[0050]

[0051] 4-Isopropyl-N-phenylbenzamide

[0052] Under an argon atmosphere, N-phenylbenzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours, and the reaction was quenched by adding saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate, and the product was separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent, and the product was obtained with a yield of 82%.

[0053] The spectroscopic data of the obtained product are as follows:

[0054] 1 1H NMR (500 MHz, CDCl3): δ = 8.15 (s, 1H), 7.79 (d, J = 8.3 Hz, 2H), 7.65 (d, J = 7.7 Hz, 2H), 7.33 (t, J = 7.9 Hz, 2H), 7.30–7.25 (m, 2H), 7.13 (t, J = 7.4 Hz, 1H), 2.96 (dt, J = 13.8, 6.9 Hz, 1H), 1.27 (d, J = 6.9 Hz, 6H).

[0055] 13 13C NMR (125 MHz, CDCl3): δ = 166.0, 152.9, 138.1, 132.4, 128.9, 127.2, 126.6, 124.3, 120.4, 77.3, 77.0, 76.8, 34.0, 23.7.

[0056] HRMS (ESI + ): calcd for C 16 H 18 NO [M + H] + 240.13884, found 240.14872.

[0057] Example 3

[0058]

[0059] 4-Isopropyl-N-(naphthalen-2-yl)benzamide

[0060] Under an argon atmosphere, N-(naphthalen-2-yl)benzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours. The reaction was quenched by adding saturated ammonium chloride aqueous solution, and extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate, and the product was separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent, and the product was obtained with a yield of 60%.

[0061] The spectroscopic data of the obtained product are as follows:

[0062] 1 H NMR (500 MHz, CDCl3): δ8.34 = (d, J = 1.5 Hz, 1H), 7.98 (s, 1H), 7.88–7.78 (m, 5H), 7.59 (dd, J = 8.8, 2.0 Hz, 1H), 7.50–7.39 (m, 2H), 7.36 (d, J = 7.9 Hz, 2H), 3.00 (dt, J = 13.8, 6.9 Hz, 1H), 1.30 (d, J = 6.9 Hz, 6H).

[0063] 13 C NMR (126 MHz, CDCl3) δ165.8, 153.3, 135.5, 133.9, 132.4, 130.7, 128.8, 127.6, 127.2, 126.9, 126.5, 125.1, 120.1, 116.9, 77.3, 77.0, 76.8, 34.1, 23.8.

[0064] HRMS (ESI + ): calcd for C 20 H 20 NO [M+H] + 290.15449, found 290.15436.

[0065] Example 4

[0066]

[0067] 4-Isopropyl-N-(4-methoxyphenyl)benzamide

[0068] Under an argon atmosphere, N-(4-methoxyphenyl)benzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours, and the reaction was quenched by adding saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate and separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent to obtain the product with a yield of 65%.

[0069] The spectroscopic data of the obtained product are as follows:

[0070] 1 1H NMR (500 MHz, CDCl3): δ = 7.80 (t, J = 11.0 Hz, 3H), 7.53 (d, J = 8.7 Hz, 2H), 7.31 (d, J = 7.5 Hz, 2H), 6.89 (d, J = 7.7 Hz, 2H), 3.81 (s, 3H), 2.97 (dt, J = 13.8, 6.9 Hz, 1H), 1.27 (d, J = 6.9 Hz, 6H).

[0071] 13 13C NMR (125 MHz, CDCl3): δ = 165.7, 156.5, 152.9, 132.5, 131.1, 127.1, 126.7, 122.1, 114.1, 77.3, 77.0, 76.8, 55.5, 34.1, 23.7.

[0072] HRMS (ESI + ): calcd for C 17 H 20 NO2 [M + H] + 270.14940, found 270.14929.

[0073] Example 5

[0074]

[0075] N-(4-fluorophenyl)-4-isopropylbenzamide

[0076] Under an argon atmosphere, N-(4-fluorophenyl)benzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours. The reaction was quenched by adding saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate and separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent to obtain the product with a yield of 70%.

[0077] The spectroscopic data of the obtained product are as follows:

[0078] 1 H NMR (500 MHz, CDCl3): δ = 7.82 (s, 1H), 7.79 (d, J = 8.2 Hz, 2H), 7.63–7.55 (m, 2H), 7.33 (d, J = 8.2 Hz, 2H), 7.05 (t, J = 8.6 Hz, 2H), 2.98 (dt, J = 13.8, 6.9 Hz, 1H), 1.28 (d, J = 6.9 Hz, 6H).

[0079] 13 C NMR (125 MHz, CDCl3): δ = 165.7, 153.3, 134.0, 132.2, 127.1, 126.9, 122.0, 115.8, 115.6, 77.3, 77.0, 76.8, 34.1, 23.7.

[0080] HRMS (ESI + ): calcd for C 16 H 17 FNO [M + H] + 258.12942, found 258.12930.

[0081] Example 6

[0082]

[0083] 4-Isopropyl-3-methoxy-N-(naphthalen-1-yl)benzamide

[0084] Under an argon atmosphere, 3-methoxy-N-(naphthalen-1-yl)benzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours. The reaction was quenched by adding saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate, and the product was separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent, and the product was obtained with a yield of 90%.

[0085] The spectral data of the obtained product are as follows:

[0086] 1 H NMR (500 MHz, CDCl3): δ = 8.32 (s, 1H), 7.98 (d, J = 7.4 Hz, 1H), 7.91–7.86 (m, 2H), 7.73 (d, J = 8.2 Hz, 1H), 7.53–7.46 (m, 5H), 7.31 (d, J = 7.8 Hz, 1H), 3.89 (s, 3H), 3.39 (dd, J = 13.8, 6.9 Hz, 1H), 1.26 (d, J = 6.9 Hz, 6H).

[0087] 13 C NMR (125 MHz, CDCl3): δ = 166.3, 157.2, 141.5, 134.1, 133.3, 132.5, 128.7, 127.5, 126.3, 126.0, 125.7, 121.2, 120.8, 118.4, 109.8, 77.3, 77.0, 76.8, 55.5, 26.8, 22.4.

[0088] HRMS (ESI + ): calcd for C 21 H 22 NO2 [M + H] + 320.16505, found 320.16493.

[0089] Example 7

[0090]

[0091] 3-Fluoro-4-isopropyl-N-(naphthalen-1-yl)benzamide

[0092] Under an argon atmosphere, 3-fluoro-N-(naphthalen-1-yl)benzamide (0.4 mmol), isopropyl chloride (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours, quenched with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate and separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent to obtain the product with a yield of 90%.

[0093] The spectral data of the obtained product are as follows:

[0094] 1 H NMR (500 MHz, CDCl3): δ = 8.24 (s, 1H), 7.93 (s, 1H), 7.90–7.85 (m, 2H), 7.73 (d, J = 8.2 Hz, 1H), 7.67 (d, J = 7.8 Hz, 1H), 7.62 (d, J = 10.7 Hz, 1H), 7.54–7.47 (m, 3H), 7.36 (t, J = 6.9 Hz, 1H), 3.32 (dt, J = 13.9, 6.9 Hz, 1H), 1.31 (d, J = 6.9 Hz, 6H).

[0095] 13 C NMR (125 MHz, CDCl3): δ = 165.1, 161.5, 159.6, 139.6, 134.1, 132.2, 128.8, 127.8, 127.4, 126.3, 126.0, 125.7, 122.6, 121.5, 120.8, 114.8, 114.5, 77.3, 77.0, 76.8, 27.3, 22.4.

[0096] HRMS (ESI + ): calcd for C 20 H 19 FNO [M + H] + 308.14507, found 308.14495.

[0097] Example 8

[0098]

[0099] 4-(Hex-2-en-1-yl)-N-(naphthalen-1-yl)benzamide

[0100] Under an argon atmosphere, N-1-naphthylbenzamide (0.4 mmol), chlorohexane (1.6 mmol), Mg (1.0 mmol), FeI2 (0.04 mmol) were added to tetrahydrofuran (1.0 mL) at room temperature. The resulting solution was stirred at room temperature for 48 hours. The reaction was quenched by adding saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate (10 mL each time, 3 times). The combined extracts were dried over anhydrous sodium sulfate and separated by column chromatography using petroleum ether∶ethyl acetate = 20∶1 as the eluent to obtain the product with a yield of 89%.

[0101] The spectroscopic data of the obtained product are as follows:

[0102] 1 H NMR (500 MHz, CDCl3): δ = 8.37 (s, 1H), 7.94–7.86 (m, 5H), 7.71 (d, J = 8.2 Hz, 1H), 7.48 (ddd, J = 12.4, 8.7, 6.6 Hz, 3H), 7.28 (d, J = 7.9 Hz, 2H), 2.78 (dt, J = 14.2, 7.0 Hz, 1H), 1.63 (dd, J = 15.2, 7.6 Hz, 2H), 1.35–1.25 (m, 6H), 1.22–1.14 (m, 1H), 0.90 (t, J = 7.2 Hz, 3H).

[0103] 13 C NMR (125 MHz, CDCl3): δ = 166.3, 152.3, 134.1, 132.5, 132.2, 128.6, 127.6, 127.3, 126.2, 125.9, 125.6, 121.4, 121.0, 77.3, 77.0, 76.8, 39.9, 37.9, 29.8, 22.7, 22.1, 14.0.

[0104] HRMS (ESI + ): calcd for C 23 H 26 NO [M + H] + 332.20144, found 332.20132.

[0105] In addition, other arylamides and secondary chloroalkanes were used to prepare the corresponding arylamide derivatives with a tertiary carbon center at the para position according to the method of the present invention, and considerable yields were obtained. It can be seen that the method of the present invention can successfully achieve the functionalization of the para C-H bond of arylamides.

[0106] As described above, it is only the specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art within the technical scope disclosed by the present invention can easily think of various equivalent modifications or substitutions, and these modifications or substitutions should all be covered within the protection scope of the present invention.

Claims

1. An arylamide derivative containing a tertiary carbon center and its preparation method, characterized in that: Under an inert atmosphere, an arylamide, a metal reducing agent, an iron catalyst, and a secondary chloroalkane are added to an organic solvent, and the reaction is carried out with stirring at room temperature. After the reaction is completed, it is quenched, separated and purified to obtain an arylamide derivative with a tertiary carbon center at the para position.

2. The preparation method according to claim 1, characterized in that: The molar ratio of the arylamide, the secondary chloroalkane, and the metal reducing agent is 1∶2 - 4∶1 - 2.5; The dosage ratio of the organic solvent to the arylamide is 2.5∶1 (mL∶mmol); The dosage of the iron catalyst is 5 - 10% of the amount of substance of the arylamide.

3. The preparation method according to claim 1 or 2, characterized in that: The reaction time is 24 - 48 h; thin layer chromatography is used for tracking during the reaction process.

4. The preparation method according to claim 3, characterized in that: The secondary chloroalkane is chloro - isopropane or 2 - chlorohexane; The metal reducing agent is aluminum, manganese, indium, magnesium or zinc; The iron catalyst is ferric chloride, ferrous chloride, ferrous bromide, ferrous iodide, iron trifluoromethanesulfonate or iron acetylacetonate; The organic solvent is tetrahydrofuran, 2 - methyltetrahydrofuran, cyclopentyl methyl ether, cyclohexane, n - hexane or 1,4 - dioxane.

5. The preparation method according to claim 4, characterized in that: The specific operation of separation and purification is to first extract with ethyl acetate, then dry with anhydrous Na2SO4, filter, reduce pressure, and finally purify by column chromatography to obtain the arylamide derivative.

6. The preparation method according to claim 1, characterized in that: When the arylamide is a compound of formula I and the secondary chloroalkane is chloro - isopropane, the product is a compound of formula I'; Among them, R1 is methyl, ethyl, isopropyl, tert - butyl, cyclohexyl, phenyl, 1 - naphthyl, 2 - naphthyl, p - methoxyphenyl or p - fluorophenyl.

7. The preparation method according to claim 1, characterized in that: When the arylamide is a compound of formula II and the secondary chloroalkane is chloro - isopropane, the product is a compound of formula II'; Among them, R2 is 3 - methyl, 3 - methoxy, 3 - fluoro, 3 - trifluoromethoxy, 3 - dimethylamino, 3,5 - dimethyl, 3,5 - difluoro or 3 - fluoro - 5 - methoxy.

8. The preparation method according to claim 1, characterized in that: When the arylamide is N - 1 - naphthylbenzamide and the secondary chloroalkane is a compound of formula III, the product is a compound of formula III'; Among them, R3 is isopropyl, isobutyl or isohexyl.

9. An arylamide derivative containing a tertiary carbon center, characterized in that: Obtained by using any one of the preparation methods of claims 1 - 8.

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