Synthesis
The general procedure for the synthesis of N,N-dimethyl-3-carboxybenzenesulfonamide from 3-chlorosulfonylbenzoic acid and dimethylamine was as follows: 3-chlorosulfonylbenzoic acid (2.60 g, 12 mmol) was dissolved in dichloromethane (DCM, 20 mL), followed by the addition of dimethylamine (2.0 M in tetrahydrofuran (THF), 20 mL, 40 mmol, 3.3 equiv). The reaction mixture was stirred at room temperature for 30 min before the reaction was quenched with 10% hydrochloric acid (HCl) solution. The reaction mixture was extracted with ethyl acetate (EtOAc) and the organic phase was washed with saturated sodium chloride (NaCl) solution and dried with anhydrous sodium sulfate (Na2SO4). Finally, the organic solvent was removed by distillation under reduced pressure to afford the target product N,N-dimethyl-3-carboxybenzenesulfonamide (1.80 g, 65% yield); mass spectrum (m/z) 229.
References
[1] ChemMedChem, 2015, vol. 10, # 9, p. 1548 - 1558
[2] Patent: WO2006/24834, 2006, A1. Location in patent: Page/Page column 82
[3] Patent: WO2006/24836, 2006, A1. Location in patent: Page/Page column 30
[4] Patent: WO2007/71963, 2007, A2. Location in patent: Page/Page column 50
[5] Patent: WO2006/40568, 2006, A1. Location in patent: Page/Page column 82
