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Method for synthesizing N-alkyl sulfonamide in water

A sulfonamide and alkyl technology, applied in the field of synthesizing N-alkylsulfonamide derivatives, can solve problems such as intractability and unsuitability for long-term storage, and achieve the effect of broad development prospects

Active Publication Date: 2020-12-08
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional method for synthesizing N-alkylsulfonamide derivatives is through the reaction of N-alkylamines with sulfonyl chlorides. However, sulfonyl chlorides are highly toxic compounds, difficult to handle, and not suitable for long-term storage

Method used

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  • Method for synthesizing N-alkyl sulfonamide in water
  • Method for synthesizing N-alkyl sulfonamide in water
  • Method for synthesizing N-alkyl sulfonamide in water

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: N-benzyl-4-methylbenzenesulfonamide

[0024] N-benzyl-4-methylbenzenesulfonamide

[0025]

[0026] 4-Methylbenzenesulfonamide (171mg, 1mmol), catalyst (7.7mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), benzyl alcohol (130mg, 1.2mmol) and water (1ml) were sequentially added to the microwave tube reaction vial. After the reaction mixture was reacted at 130°C for 2 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), with a yield of 91%.

[0027] 1 H NMR (500MHz, CDCl 3 )δ7.74 (d, J=8.4Hz, 2H, ArH), 7.29-7.23 (m, 5H, ArH), 7.19-7.17 (m, 2H, ArH), 4.99 (br s, 1H, NH), 4.09 (d, J=6.0Hz, 2H, CH 2 NH); 13 C NMR (125MHz, CDCl 3 ) δ 143.4, 136.8, 136.3, 129.7, 128.6, 127.81, 127.78, 127.1, 47.2, 21.4.

Embodiment 2

[0028] Embodiment 2: N-(2-methylbenzyl)-4-methylbenzenesulfonamide

[0029] N-(2-methylbenzyl)-4-methylbenzenesulfonamide

[0030]

[0031] 4-Methylbenzenesulfonamide (171mg, 1mmol), catalyst (7.7mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), benzyl alcohol (130mg, 1.2mmol) and water (1ml) were sequentially added to the microwave tube reaction vial. After the reaction mixture was reacted at 130°C for 2 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), with a yield of 83%.

[0032] 1H NMR (500MHz, CDCl3) δ7.74(d, J=8.2Hz, 2H), 7.28(d, J=8.1Hz, 2H), 7.15(t, J=7.0Hz, 1H), 7.11-7.06(m ,3H),4.06(s,2H),2.43(s,3H),2.23(s,3H); 13C NMR(125MHz,CDCl3)δ143.4,136.6,133.9,130.5,129.7,128.8,128.1,127.1,126.1, 45.3, 21.4, 18.7...

Embodiment 3

[0033] Embodiment 3: N-(4-methylbenzyl)-4-methylbenzenesulfonamide

[0034] N-(4-Methylbenzyl)-4-methylbenzenesulfonamide

[0035]

[0036] 4-methylbenzenesulfonamide (171mg, 1mmol), catalyst (7.7mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), 4-methylbenzyl alcohol (146.6mg, 1.2mmol) and water (1ml) were sequentially added to the microwave tube. After the reaction mixture was reacted at 130°C for 2 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), with a yield of 82%.

[0037] 1H NMR (500MHz, CDCl3) δ7.74 (d, J = 7.7Hz, 2H), 7.29 (d, J = 7.8Hz, 2H), 7.06 (s, 4H), 4.85 (br s, 1H), 4.05 ( s, 2H), 2.43 (s, 3H), 2.30 (s, 3H); 13C NMR (125MHz, CDCl3) δ 143.8, 143.2, 139.5, 136.6, 129.8, 128.5, 127.5, 127.0, 46.4, 44.4, 21.5.

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Abstract

The invention discloses a method for synthesizing N-alkyl sulfonamide in water, in particular to a method for synthesizing an N-alkyl sulfonamide derivative from a sulfonamide derivative and alcohol,and a water-soluble iridium complex is adopted to catalyze the reaction of N-alkyl sulfonamide. Compared with the previous synthesis method, the method has the advantages that a reaction equivalent substrate is used in the reaction process, so that raw material waste is avoided; weak base is used, and reaction conditions are mild; non-toxic and harmless pure water is used as a solvent in the reaction, only water is generated as a by-product, the atom reaction economy is high, and the requirement of green chemistry is met.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing N-alkylsulfonamide derivatives. Background technique [0002] N-Alkylsulfonamide derivatives represent an important class of nitrogen-containing compounds, exhibiting a wide range of physiological and pharmacological activities. For example, such compounds are used as secreted frizzled-related protein 1 (SFRP-1) inhibitors, potent thromboxane receptor antagonists, Mycobacterium tuberculosis inhibitors and antineoplastic prodrugs, among others. ((a) A. Gopalsamy, M. Shi, B. Stauffer, R. Bahat, J. Billiard, H. Ponce-de-Leon, L. Seestaller-Wehr, S. Fukayama, A. Mangine, R. Moran, G. Krishnamurthy, P. Bodine, J. Med. Chem. 2008, 51, 7670-7672; b) C. Ballatore, J. H. Soper, F. Piscitelli, M. James, L. Huang, O. Atasoylu, D. M. Huryn, J.Q. Trojanowski, V.M.Y. Lee, K.R. Brunden, A.B. Smith, J. Med. Chem. 2011, 54, 6969-6983; c)...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/16C07C311/17C07C311/29C07C311/03C07C311/14C07C311/13
CPCC07C303/40C07C2601/02C07C311/16C07C311/17C07C311/29C07C311/03C07C311/14C07C311/13
Inventor 李峰艾瑶胥婧孟冲
Owner NANJING UNIV OF SCI & TECH
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