Synthesis method of N-diarylmethyl sulfonamide compound

A technology of diarylmethylsulfonamide and synthesis method, applied in the formation/introduction of sulfonyl/sulfinyl groups, preparation of sulfonamide, organic chemistry, etc., to achieve the effect of simple operation and economical raw materials

Active Publication Date: 2020-05-19
内蒙古赤峰市柏善医药有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

This reaction strategy can avoid a large number of waste by-products, and the raw materials are simple and easy to obtain. So far, there has been no literature report

Method used

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  • Synthesis method of N-diarylmethyl sulfonamide compound
  • Synthesis method of N-diarylmethyl sulfonamide compound
  • Synthesis method of N-diarylmethyl sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of N-(2,4,6-trimethoxyphenyl) benzylsulfonamide

[0030]

[0031] Benzaldehyde (106mg, 1.0mmol), 1 equivalent of p-toluenesulfonamide (171mg, 1.0mmol), FeCl 3 (16 mg, 0.1 mmol) and 1 equivalent of 1,3,5-trimethoxybenzene (168 mg, 1.0 mmol) were added to DCE (2 mL). The reaction was stirred at room temperature for 8 hours. After the reaction was completed, it was separated by column chromatography, and the eluting agent was a mixed solution of petroleum ether:ethyl acetate 2:1 to obtain 393 mg of a white solid product with a yield of 92%.

[0032] Its NMR data are as follows:

[0033] Such as figure 1 as shown, 1 H NMR (400MHz, CDCl 3 )7.50(d, J=8.4Hz, 2H), 7.26-7.15(m, 5H), 7.00(d, J=8.4Hz, 2H), 6.24(d, J=10.4Hz, 1H), 6.10(d, J=11.2Hz, 1H), 5.88(s, 2H), 3.72(s, 3H), 3.61(s, 6H), 2.30(s, 3H);

[0034] Such as figure 2 as shown, 13 C NMR (100MHz, CDCl 3 )160.8,157.8(2C),142.3,141.3,137.6,128.6(2C),127.8(2C),126.8,126.5(2C),126.4(2...

Embodiment 2

[0035] Embodiment 2: the synthesis of N-(2,4,6-trimethoxyphenyl) p-chlorobenzylsulfonamide

[0036]

[0037] P-chlorobenzaldehyde (140mg, 1.0mmol), 1 equivalent of p-toluenesulfonamide (171mg, 1.0mmol), FeCl 3 (16 mg, 0.1 mmol) and 1 equivalent of 1,3,5-trimethoxybenzene (168 mg, 1.0 mmol) were added to DCE (2 mL). The reaction was stirred at room temperature for 6 hours. After the reaction was completed, it was separated by column chromatography, and the eluent was a mixed solution of petroleum ether:ethyl acetate 2:1 to obtain 428 mg of a white solid product with a yield of 93%.

[0038] Its NMR data are as follows:

[0039] Such as image 3 as shown, 1 H NMR (400MHz, CDCl 3 )7.49(d, J=7.6Hz, 2H), 7.19-7.14(m, 4H), 7.00(d, J=7.6Hz, 2H), 6.23(d, J=10.8Hz, 1H), 6.06(d, J=10.4Hz, 1H), 5.88(s, 2H), 3.73(s, 3H), 3.61(s, 6H), 2.29(s, 3H);

[0040] Such as Figure 4 as shown, 13 C NMR (100MHz, CDCl 3 )2161.0,157.7(2C),142.5,140.0,137.4,131.2,128.7(2C),127.9(2C),127.8(2...

Embodiment 3

[0041] Embodiment 3: the synthesis of N-(2,4,6-trimethoxyphenyl) p-nitrobenzylsulfonamide

[0042]

[0043] P-chlorobenzaldehyde (140mg, 1.0mmol), 1 equivalent of p-toluenesulfonamide (171mg, 1.0mmol), FeCl 3 (16 mg, 0.1 mmol) and 1 equivalent of 1,3,5-trimethoxybenzene (168 mg, 1.0 mmol) were added to DCE (2 mL). The reaction was stirred at room temperature for 12 hours. After the reaction was completed, it was separated by column chromatography, and the eluting agent was a mixed solution of petroleum ether:ethyl acetate 1:1 to obtain 448 mg of a white solid product with a yield of 95%.

[0044] Its NMR data are as follows:

[0045] Such as Figure 5 as shown, 1 H NMR (300MHz, CDCl3 )8.03(d, J=9.2Hz, 2H), 7.54(d, J=8.4Hz, 2H), 7.44(d, J=8.8Hz, 2H), 7.04(d, J=8.0Hz, 2H), 6.48 (d,J=10.8Hz,1H),6.16(d,J=10.8Hz,1H),5.90(s,2H),3.73(s,3H),3.62(s,6H),2.31(s,3H) ;

[0046] Such as Figure 6 as shown, 13 C NMR (75MHz, CDCl 3 )161.3,157.5(2C),149.4,146.5,142.7,137.1,128.7(2...

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Abstract

The invention discloses a synthesis method of an N-diarylmethyl sulfonamide compound, and belongs to the technical field of organic synthesis intermediates. According to the synthesis method, the N-diarylmethyl sulfonamide compound is synthesized by utilizing a cascade reaction; the method specifically comprises the following steps: (1) adding an aromatic aldehyde, a sulfonamide, trimethoxybenzeneor a derivative thereof, and Lewis acid into a reaction tube according to a molar ratio of 1.0: 1.0: 1.0: 0.1, and carrying out magnetic stirring reaction at room temperature for 8-24 hours by taking1, 2-dichloroethane as a solvent; and (2) after the reaction is finished, evaporating under reduced pressure to remove most of the solvent, and carrying out column chromatography separation and purification on a residual mixed solution by using petroleum ether and ethyl acetate in a volume ratio of (1: 1)-(2: 1) as leacheate to obtain the product. The N-diarylmethyl sulfonamide compound synthesized by the method has wide application in the fields of medicines, pesticides and the like. The synthesis method disclosed by the invention has the advantages of low cost, simplicity in operation, highyield, mild conditions and the like, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis intermediates, and in particular relates to a method for synthesizing an N-diarylmethylsulfonamide compound through series reactions. Background technique [0002] N-diarylmethylsulfonamide compounds are very important intermediates in organic synthesis. It can be transformed into triaryl methane compounds, benzyl substituted amine compounds and inden compounds by leaving the amino group. For example, triarylmethanes are an important class of organic dyes commonly used in optoelectronic materials. In addition, such compounds can efficiently synthesize a series of biologically and pharmacologically active substances, including pyrazoles, oxazoles, thiazoles, quinolinones, 1,4-tetrahydropyridines, benzopyrans, diazepines, etc. These compounds can also exist as basic molecular skeletons in biological and pharmaceutically active natural or artificial products. [0003] In recent years, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/40C07C311/17C07B45/04
CPCC07C303/40C07B45/04C07C311/17
Inventor 黄达云李隆隆
Owner 内蒙古赤峰市柏善医药有限公司
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