Dimethylamine → N,N-dimethyl-4-sulfamoylbenzamide

참여 물질

반응 단계

To a solution of 4-carboxybenzenesulfonamide (5 g; 24.8 mmol; 1 eq) in THF (75 mL) at 0° C. is added in one portion 1,1′-carbonyl diimidazole (4.8 g; 29.8 mmol; 1.2 eq) and the reaction mixture is stirred for 3 h at room temperature. A solution of dimethylamine (37.3 mL; 2 M; 74.6 mmol; 3 eq) in THF is added dropwise over 20 min and the reaction mixture is stirred at room temperature for 1 h. The solvent is removed under reduced pressure and the residue is diluted with EtOAc (100 mL) and the organic phase is washed with a 10% solution of NaHCO3 (30 mL). The white precipitate formed in the aqueous phase is filtered off, washed with water and dried under vacuum to afford 4.1 g (72%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.86 (d, J=8.3 Hz, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.45 (s, 2H), 3.00 (s, 3H), 2.88 (s, 3H). HPLC (max plot) 99%; Rt 1.07 min. LC/MS: (ES+): 229.0.

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