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A kind of method for synthesizing n-alkylsulfonamide derivatives

A ‐alkylsulfonamide and derivative technology, applied in the field of N-alkylsulfonamide derivatives, can solve problems such as low yield, and achieve the effect of broad development prospects

Inactive Publication Date: 2016-05-18
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction requires the use of an equivalent amount of base, and the yield of the reaction is very low (<72% yield), especially when the substrate contains electron-withdrawing groups, the yield is only 25% (Saidi, O.; Blacker, A.J.; Lamb, G.W. ; Marsden, S.P.; Taylor, J.E.; Williams, J.M.J. Org. Process Res. Dev. 2010, 14, 1046.)

Method used

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  • A kind of method for synthesizing n-alkylsulfonamide derivatives
  • A kind of method for synthesizing n-alkylsulfonamide derivatives
  • A kind of method for synthesizing n-alkylsulfonamide derivatives

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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 A (8.3mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), benzyl alcohol (130mg, 1.2mmol) and Water (1ml) was sequentially added to a 25ml Schlenk reaction flask. After the reaction mixture was reacted at 120°C for 15 hours, it was cooled to room temperature. A large amount of precipitation was separated out, and the water was removed by filtration, and the filter cake was washed with water for 3 times to obtain the target compound, the yield: 92%

[0027] 1 HNMR (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(brs,1H,NH),4.09( d,J=6.0Hz,2H,CH 2 NH); 13 CNMR (125MHz, CDCl 3 )δ143.4, 136.8, 136.3, 129.7, 128.6, 127.81, 127.78, 127.1, 47.2, 21.4.

Embodiment 2

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

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

[0030]

[0031]4-methylbenzenesulfonamide (171mg, 1mmol), catalyst A (8.3mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), 4-methylbenzyl alcohol (146mg, 1.2mmol) and water (1ml) were sequentially added to a 25ml Schlenk reaction flask. After the reaction mixture was reacted at 120°C for 15 hours, it was cooled to room temperature. A large amount of precipitation was separated out, and the water was removed by filtration, and the filter cake was washed with water for 3 times to obtain the target compound, the yield: 87%

[0032] 1 HNMR (500MHz, CDCl 3 )δ7.74(d,J=8.2Hz,2H,ArH),7.29(d,J=8.2Hz,2H,ArH),7.06(s,4H,ArH),4.83(brs,1H,NH),4.05 (d,J=5.4Hz,2H,CH 2 NH),2.43(s,3H,CH 3 ),2.30(s,3H,CH 3 ); 13 CNMR (125MHz, CDCl 3 )δ143.4, 137.6, 136.8, 133.2, 129.7, 129.3, 127.8, 127.1, 47.0, 21.5, 21.0.

Embodiment 3

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

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

[0035]

[0036] 4-methylbenzenesulfonamide (171mg, 1mmol), catalyst A (8.3mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), 4-isopropylbenzyl alcohol (180mg , 1.2mmol) and water (1ml) were sequentially added to a 25ml Schlenk reaction flask. After the reaction mixture was reacted at 120°C for 15 hours, it was cooled to room temperature. A large amount of precipitation was separated out, and the water was removed by filtration, and the filter cake was washed with water for 3 times to obtain the target compound, the yield: 81%

[0037] 1 HNMR (500MHz, CDCl 3 )δ7.75(d,J=8.2Hz,2H,ArH),7.30(d,J=8.1Hz,2H,ArH),7.12(quart,J=8.0Hz,4H,ArH),4.56(brs,1H ,NH),4.09(t,J=2.9Hz,2H,CH 2 NH),2.91-2.82(heptet,J=6.9Hz,1H,CH),2.44(s,3H,CH 3 ),1.21(d,J=7.0Hz,6H,2xCH 3 ); 13 CNMR (125MHz, CDCl 3 )δ148.7, 143.4, 137.0, 133.6, 129.7, 128.0, 12...

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Abstract

The invention discloses a method for synthesizing a N-alkyl sulfonamide derivative. The method comprises the following steps: adding a sulfonamide derivative, a water-soluble catalyst, an alkali, alcohol and a solvent into a reaction container; reacting the reaction mixture at 100-120 DEG C for several hours, cooling to room temperature; performing rotary evaporation to remove the solvent, and then separating by a column to obtain the target compound. The method of the invention starts from the sulfonamide derivative, and obtains the N-alkyl sulfonamide derivative through reaction with alcohol. The method of the invention adopts a water-soluble iridium complex as a catalyst; the reaction is carried out in water; and the target compound is obtained with a high yield. Therefore, the reaction meets the requirements for green chemistry, and the method has wide development prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a method for 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. Chem.2012, 55, 553-557; d) R.J.Stevenson, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C303/40C07C311/16C07C311/17C07D333/20C07C311/29C07C311/03C07C311/14C07C311/13
Inventor 李峰渠攀攀孙春楼马娟
Owner NANJING UNIV OF SCI & TECH