Amino-(N-alkyl) benzsulfamide synthesis method

A technology for aminobenzenesulfonamide and amino synthesis, which is applied in the preparation of sulfonic acid amides, chemical instruments and methods, organic chemistry, etc., can solve problems such as low atom economy, and achieve broad development prospects and high economy effects.

Inactive Publication Date: 2016-11-23
NANJING UNIV OF SCI & TECH
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AI Technical Summary

Problems solved by technology

[0003] The traditional method of synthesizing amino-(N-alkyl)benzenesulfonamide is through multi-step reaction

Method used

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  • Amino-(N-alkyl) benzsulfamide synthesis method

Examples

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 an amino-(N-alkyl) benzsulfamide synthesis method. The method comprises the steps of adding aminobenzenesul fonamide, an iridium complex catalyst, alkali, compound alcohol and the solvent tert-amyl alcohol into a reaction container for reaction lasting several hours at 120-150 DEG C, then reducing temperature to room temperature, conducting rotary evaporation to remove the solvent, and then conducting column separation to obtain the target compound. Commercial aminobenzenesul fonamide and nearly non-toxic compound alcohol are used as starting materials, only water is generated as reaction byproduct, and no environment harm is done; reaction atom economy is high.

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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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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