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Aryl sulfonamide tertiary amine compound synthesizing method

A technology of arylsulfonyl tertiary amide and synthesis method, which is applied in the preparation of sulfonic acid amide, the formation/introduction of sulfonyl group/sulfinyl group, organic chemistry, etc., can solve the problem of large-scale preparation and many reaction steps that are not suitable for industrialization. problem, to achieve the effect of low cost, convenient operation and simple synthesis process

Active Publication Date: 2018-04-24
山东中新科农生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has many reaction steps and is not suitable for industrialized large-scale preparation.

Method used

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  • Aryl sulfonamide tertiary amine compound synthesizing method
  • Aryl sulfonamide tertiary amine compound synthesizing method
  • Aryl sulfonamide tertiary amine compound synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, the synthesis of N,N-dimethyl-4-methylbenzenesulfonamide

[0023] Use a flame-dried 50ml two-neck flask, replace the nitrogen three times, use a syringe to dissolve p-toluenesulfonyl chloride (190mg, 1mmol) in acetonitrile (3ml) into the cooled reaction flask, heat the acetonitrile solution to reflux Finally, dissolve N,N,N,N-tetramethylethylenediamine (139mg, 1.2mmol) in 3ml of anhydrous acetonitrile, and slowly add it dropwise to the reaction bottle filled with p-toluenesulfonyl chloride with a syringe , then reacted for 1 hour under acetonitrile reflux, removed the heating, evaporated the solvent under reduced pressure, and separated by flash column chromatography to obtain 183 mg of the product, with a yield of 92%. Its synthetic formula is as follows:

[0024]

[0025] Spectral data: 1 H NMR (600 MHz, CDCl 3 ) δ (ppm): 7.66 (d, J = 8.2 Hz, 2H), 7.33(d, J = 8.0 Hz, 2H), 2.68 (s, 6H), 2.43 (s, 3H); 13 C NMR (151 MHz, CDCl 3 ) δ (ppm): 143.4,...

Embodiment 2

[0026] Embodiment 2, the synthesis of N, N-diethyl-p-toluenesulfonamide

[0027] Use a flame-dried 50ml two-neck flask, replace the nitrogen three times, use a syringe to dissolve p-toluenesulfonyl chloride (190mg, 1mmol) in acetonitrile (3ml) into the cooled reaction flask, heat the acetonitrile solution to reflux Finally, dissolve N,N,N,N-tetraethylethylenediamine (206mg, 1.2mmol) in 3ml of anhydrous acetonitrile, and slowly add it dropwise to the reaction bottle containing p-toluenesulfonyl chloride with a syringe , then reacted for 1 hour under acetonitrile reflux, removed the heat, evaporated the solvent under reduced pressure, and separated by flash column chromatography to obtain 197 mg of the product with a yield of 87%. Its synthetic formula is as follows:

[0028]

[0029] Spectral data: 1 H NMR (600 MHz, CDCl 3 ) δ (ppm): 7.68 (d, J = 8.2 Hz, 2H), 7.27(d, J = 8.0 Hz, 2H), 3.21 (q, J = 7.2 Hz, 4H), 2.41 (s, 3H), 1.11 (t, J = 7.1Hz, 6H); 13 C NMR (151 M...

Embodiment 3

[0030] Embodiment 3, N, the synthesis of N-dipropyl p-toluenesulfonamide

[0031] Use a flame-dried 50ml two-neck flask, replace nitrogen three times, use a syringe to dissolve p-toluenesulfonyl chloride (190mg, 1mmol) in acetonitrile (3ml) into the cooled reaction flask, heat the acetonitrile solution to reflux Finally, dissolve N,N,N,N-tetraisobutylethylenediamine (273mg, 1.2mmol) in 3ml of anhydrous acetonitrile, and slowly add it dropwise to the reaction mixture containing p-toluenesulfonyl chloride bottle, then reacted for 1 hour under acetonitrile reflux, removed the heat, evaporated the solvent under reduced pressure, and separated by flash column chromatography to obtain 216 mg of the product, with a yield of 85%. Its synthetic formula is as follows:

[0032]

[0033] Spectral data: 1 H NMR (600 MHz, CDCl 3 ) δ (ppm): 7.68 (d, J = 8.3 Hz, 2H), 7.27(d, J = 16.4 Hz, 2H), 3.05 (dd, J= 8.5, 6.9 Hz, 4H), 2.41 (s, 3H), 1.59 –1.49 (m, 4H), 0.86 (t, J = 7.4 Hz, 6H...

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Abstract

The invention provides an aryl sulfonamide tertiary amine compound synthesizing method. According to the method, in an anhydrous aprotic solvent and under nitrogen protection, acryl sulfonyl chlorideand di-tertiary amine react for 1 to 12 hours according to a molar ratio of (1 to 1) to (1 to 20) under the condition of 50 to 150 DEG C, and the aryl sulfonamide tertiary amine compound can be obtained by purification. According to the method disclosed by the invention, the acryl sulfonyl chloride and the di-tertiary amine can directly generate C-S bond formation in the aprotic solvent and generate C-N bond breakage at the same time. According to the one-step aryl sulfonamide synthesizing method, raw materials are easy to obtain, a synthesizing technology is simple, operation is convenient, cost is low, and yield is high.

Description

technical field [0001] The invention relates to a synthesis method of arylsulfonyl tertiary amine compounds, in particular to a method for synthesizing arylsulfonyl tertiary amines through the direct reaction of arylsulfonyl chloride and di-tertiary amine, which belongs to the technical field of chemical synthesis. Background technique [0002] Sulfonamide compounds have a variety of biological activities. For example, as antibacterial drugs in clinical practice, sulfonamide drugs have the advantages of broad antibacterial spectrum, stable properties, easy use, and low price. They are currently commonly used antibacterial drugs next to antibiotics. In addition, since sulfonamide compounds are widely used in various fields such as pesticides and materials, their synthesis methods have been continuously developed. [0003] Tertiary sulfonylamide is a kind of compound with special structure among sulfonamide compounds, and its structural formula is as follows: [0004] [0...

Claims

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Application Information

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IPC IPC(8): C07C303/38C07D295/26C07C311/16C07C311/21C07B45/04
CPCC07B45/04C07C303/38C07D295/26C07C311/16C07C311/21
Inventor 傅颖徐勤善李全周
Owner 山东中新科农生物科技有限公司
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