Method for synthesizing N-aryl formamide compound

A technology for aryl formamides and compounds, which is applied in the field of synthesizing N-aryl formamides and their derivatives, can solve the problems of no advantage in atom economy and contrary to environmental protection, achieve good functional group tolerance, reduce environmental pollution, and be good The effect of applying the foreground

Inactive Publication Date: 2018-11-06
XIJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In summary, the traditional methods of synthesizing amides mostly use stoichiometric toxic reagents or produce a large amount of by-products and chemical wastes in the reaction process, which not only has no advantage in atom economy, but also runs counter to environmental protection

Method used

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  • Method for synthesizing N-aryl formamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A method for synthesizing 4-bromo-N-methylbenzamide, the steps are:

[0028] Step 1: Weighing

[0029] Weigh CuCl1.0mg (0.01mmol), salicylic acid 1.4mg (0.01mmol), NaBF 4 16.5mg (0.15mmol), 4-bromo-N,N-dimethylaniline 200mg (0.01mmol);

[0030] Step 2: Weigh 1.0 mL of acetonitrile and add it to the Scheck tube, and add the CuCl, salicylic acid, NaBF 4 and 4-bromo-N,N-dimethylaniline were put into acetonitrile, and stirred at 30°C for 48 hours under an oxygen atmosphere. After the reaction was completed, 10 mL of distilled water was added to the mixture, and then extracted three times with 15 mL of dichloromethane, and collected Organic phase, with anhydrous Na 2 SO 4 Dry, filter with suction, remove dichloromethane with a rotary evaporator, and separate by column chromatography to obtain a white solid 4-bromo-N-methylbenzamide with a yield of 60%, a white solid, m.p.61.1-66.1°C. Spectral data is: Main structure: 1 H NMR (400MHz, CDCl 3 )δ: 8.45(s, 1H), 7.52(d, J=...

Embodiment 2

[0032] A kind of method of synthesizing 4-chloro-N-methylbenzamide, its step is

[0033] Step 1: Weighing

[0034] Weigh CuCl1.0mg (0.01mmol), salicylic acid 1.4mg (0.01mmol), NaBF 4 16.5mg (0.15mmol), 4-chloro-N,N-dimethylaniline 200mg (0.01mmol);

[0035] Step 2: Weigh 1.0 mL of acetonitrile and add it to the Scheck tube, and add the CuCl, salicylic acid, NaBF 4 and 4-chloro-N,N-dimethylaniline were put into acetonitrile, and stirred at 30°C for 45 hours under an oxygen atmosphere. After the reaction was completed, 10 mL of distilled water was added to the mixture, and then extracted three times with 15 mL of dichloromethane, and collected Organic phase, with anhydrous Na 2 SO 4 Drying, suction filtration, removal of dichloromethane with a rotary evaporator, separation by column chromatography to obtain a white solid 4-chloro-N-methylbenzamide, the yield is 63%, and the spectral data are: 1 H NMR (400MHz, CDCl 3 )δ: 8.46(s, 1H), 7.53(d, J=8.0Hz, 2H), 7.06(d, J=8.8Hz, 2...

Embodiment 3

[0038] A kind of method for synthesizing 4-fluoro-N-methylbenzamide, its step is

[0039] Step 1: Weighing

[0040] Weigh CuCl1.0mg (0.01mmol), salicylic acid 1.4mg (0.01mmol), NaBF 4 16.5mg (0.15mmol), 4-fluoro-N,N-dimethylaniline 200mg (0.01mmol);

[0041] Step 2: Weigh 1.0 mL of acetonitrile and add it to the Scheck tube, and add the CuCl, salicylic acid, NaBF 4 and 4-fluoro-N,N-dimethylaniline were put into acetonitrile, stirred at 35°C for 40 hours under an oxygen atmosphere, and the reaction was completed; 10 mL of distilled water was added to the mixture, and extracted three times with 15 mL of dichloromethane, Organic phase, with anhydrous Na 2 SO 4 Dry, filter with suction, remove methylene chloride with a rotary evaporator, and separate by column chromatography to obtain oily 4-fluoro-N-methylbenzamide, with a yield of 52%, and the spectral data are: 1 H NMR (400MHz, CDCl 3 )δ: 8.37(s, 1H), 7.15-7.05(m, 4H), 3.28(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ: 162.2, 16...

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Abstract

A method for synthesizing an N-aryl formamide compound comprises the following steps: putting an N, N-dimethylaniline compound, cuprous chloride, sodium tetrafluoroborate and salicylic acid in an organic solvent in an oxygen atmosphere, reacting for 0.5-48 hours at 30-60 DEG C, and separating and purifying a product to obtain the N-aryl formamide compound, wherein the using amount of the organic solvent is as follows: the amount-of-substance concentration of the N, N-dimethylaniline compound, the cuprous chloride, the sodium tetrafluoroborate and the salicylic acid is 0.5-1mol / L. The method has the advantages as follows: the operation is simple, a used catalyst is cheap, a reaction condition is mild, the product yield is high, the defects of expensive raw material reagents, a harsh condition, cumbersome synthesis steps, not high total yield and the like in the prior art are overcome, and a good application prospect is achieved.

Description

technical field [0001] The invention belongs to the technical field of synthesizing N-aryl formamides and derivatives thereof, and in particular relates to a method for synthesizing N-aryl formamides. Background technique [0002] Amide compounds and their derivatives are widely found in natural products, pharmaceuticals, industrial chemicals, medical and functional materials, and various synthetic fibers composed of polyamides. Especially in the synthesis of biochemical substances or fine chemical products, it plays a very important role. Compounds containing amide bonds are essential constituents in medicinal chemistry. In existing medicinal chemistry databases, more than 25% of the core structural fragments of known drugs contain amide bonds, and they exhibit high biological activity. Amides with different structures have different biological activities, which play an important role in maintaining human life and health. The formation of amide bonds is an important react...

Claims

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Application Information

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IPC IPC(8): C07B43/06C07C231/10C07C233/15C07C233/33C07C233/54C07C233/03C07C233/25C07C253/30C07C255/60C07C315/04C07C317/40
CPCC07B43/06C07C231/10C07C253/30C07C315/04C07C233/15C07C233/33C07C233/54C07C233/03C07C233/25C07C255/60C07C317/40
Inventor 刘玉霞姜雪王煜婷贺振振
Owner XIJING UNIV
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