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A method for synthesizing amino-(n-alkyl) benzenesulfonamides

A technology of aminobenzenesulfonamide and benzenesulfonamide, which is applied in the preparation of sulfonic acid amide, chemical instruments and methods, organic chemistry, etc., can solve problems such as low atomic economy, and achieve the effect of broad development prospects and high economy.

Inactive Publication Date: 2018-01-23
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] The traditional method of synthesizing amino-(N-alkyl)benzenesulfonamide is through multi-step reaction, which can be realized by using a large amount of toxic reagents, and the atom economy of the reaction is low

Method used

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  • A method for synthesizing amino-(n-alkyl) benzenesulfonamides
  • A method for synthesizing amino-(n-alkyl) benzenesulfonamides
  • A method for synthesizing amino-(n-alkyl) benzenesulfonamides

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: 4-amino-N-benzylbenzenesulfonamide

[0022] 4-amino-N-benzylbenzenesulfonamide

[0023]

[0024] Under nitrogen protection, 4-aminobenzenesulfonamide (172mg, 1mmol), [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), cesium carbonate (65mg, 0.2mmol), benzyl alcohol (130mg, 1.2mmol), and tert-amyl alcohol (1mL) were sequentially added to a 25mL Schlenk reaction flask. After the mixture was reacted at 120°C for 12 hours, it was cooled to room temperature, and the solvent was removed under reduced pressure in vacuo. Then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / n-hexane), yield: 88%.

[0025] 1 H NMR (500MHz, DMSO-d 6 )δ7.62(br s,1H,NH),7.44(d,J=8.6Hz,2H,ArH),7.31-7.20(m,5H,ArH),6.60(d,J=8.6Hz,2H,ArH ),5.92(s,2H,NH 2 ),3.87(s,2H,NCH 2 ); 13 C NMR (125MHz, DMSO-d 6 )δ152.4, 138.0, 128.4, 127.5, 127.0, 125.6, 112.6, 46.0.

Embodiment 2

[0026] Embodiment 2: N-(4-methylbenzyl)-4-aminobenzenesulfonamide

[0027] N-(4-methylbenzyl)-4-aminobenzenesulfonamide

[0028]

[0029] Under nitrogen protection, 4-aminobenzenesulfonamide (172mg, 1mmol), [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), cesium carbonate (65mg, 0.2mmol), p-methylbenzyl alcohol (147mg, 1.2mmol), and tert-amyl alcohol (1.0mL) were sequentially added to a 25mL Schlenk reaction flask. After the mixture was reacted at 120°C for 12 hours, it was cooled to room temperature, and the solvent was removed under reduced pressure in vacuo. Then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / n-hexane), yield: 86%.

[0030] 1 H NMR (500MHz, DMSO-d 6 )δ7.55(br s,1H,NH),7.43(d,J=8.6Hz,2H,ArH),7.10(q,J=7.4Hz,4H,ArH),6.60(d,J=8.6Hz, 2H,ArH),5.91(s,2H,NH 2 ),3.81(s,2H,NCH 2 ),2.26(s,3H,CH 3 ); 13 C NMR (125MHz, DMSO-d 6 )δ152.4,136.0,135.0,128.7,128.4,127.5,125.6,112.6,45.8,20.6; HRMS-EI(70eV)m / z calcd for C...

Embodiment 3

[0031] Embodiment 3: N-(4-isopropylbenzyl)-4-aminobenzenesulfonamide

[0032] N-(4-isopropylbenzyl)-4-aminobenzenesulfonamide

[0033]

[0034] Under nitrogen protection, 4-aminobenzenesulfonamide (172mg, 1mmol), [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), cesium carbonate (65mg, 0.2mmol), p-cymenyl alcohol (180mg, 1.2mmol), and tert-amyl alcohol (1.0mL) were sequentially added to a 25mL Schlenk reaction flask. After the mixture was reacted at 120°C for 12 hours, it was cooled to room temperature, and the solvent was removed under reduced pressure in vacuo. Then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / n-hexane), yield: 80%.

[0035] 1 H NMR (500MHz, DMSO-d 6 )δ7.55(br s,1H,NH),7.43(d,J=8.5Hz,2H,ArH),7.14(s,4H,ArH),6.60(d,J=8.5Hz,2H,ArH), 5.91(s,2H,NH 2 ),3.82(s,2H,NCH 2 ), 2.90-2.79 (heptet, J=6.9Hz, 1H, CH), 1.17 (d, J=7.0Hz, 6H, 2xCH 3 ); 13 C NMR (125MHz, DMSO-d 6)δ152.4,147.2,135.3,128.4,127.6,126.0,125.6,1...

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Abstract

The invention discloses a method for synthesizing amino-(N-alkyl)benzenesulfonamide. Including the following steps: in a reaction vessel, add aminobenzenesulfonamide, iridium complex catalyst, alkali, compound alcohol, solvent tert-amyl alcohol, react the reaction mixture at 120-150 o C for several hours, cool to room temperature, and rotate to evaporate Removal of the solvent followed by column separation afforded the title compound. The invention uses commercialized aminobenzenesulfonamide and almost non-toxic compound alcohol as starting materials; the reaction only generates water as a by-product, without environmental hazard; and the reaction atom is economical.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing amino-(N-alkyl)benzenesulfonamides. Background technique [0002] N-Alkylsulfonamide derivatives represent an important class of nitrogen-containing compounds, exhibiting a wide range of physiological and pharmacological activities. ((a) Bissinger, E.M.; Heinke, R.; Spannhoff, A.; Eberlin, A.; Metzger, E.; Cura, V.; Hassenboehler, P.; Cavarelli, J.; Schüle, R.; Bedford, M.T.; Sippl, W.; Jung, M. Bioorg. Med. Chem. 2001, 19, 3717. (b) Ghosh, A.K.; Chapsal, B.D.; Y.; Amano, M.; Weber, I.T.; Mitsuya, H.J. Med. Chem. 2011, 54, 5890. (c) Agniswamy, J.; Shen, C.; Wang, Y.; ; Xu, C.; Sayer, J.M.; Louis, J.M.; Weber, I.T.J.Med.Chem.2013, 56, 4017. (d) Ghosh, A.K.; Agniswamy, J.; Wang, Y.; Amano, M.; Weber, I.T.; Mitsuya, H.J. Med. Chem. 2013, 56, 6792.) [0003] The traditional method of synthesizing amino-(N-alkyl)benzenesulf...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/40C07C311/39C07C311/40C07C311/43C07F17/02C07D333/20
Inventor 李峰陆磊马娟
Owner NANJING UNIV OF SCI & TECH
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