Dimethylamine → 3,4-Dimethoxy-N-[4-(3-nitrophenyl)-5-dimethylaminomethyl-1,3-thiazole-2-yl]benzenesulfonamide

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To a stirred solution of 3,4-dimethoxy-N-(4-(3-nitrophenyl)thiazol-2-yl)benzenesulfonamide (0.267 g, 0.68 mmol) in ethanol (10 mL, warming required) was added an aqueous solution of formaldehyde (37%, 0.5 mL, about 0.194 g, 6.5 mmol) followed by the dropwise addition of a solution of dimethylamine in water (60 wt %, 55 mL, about 0.274 g, 6.1 mmol). The addition was slightly exothermic, and the pale yellow solution became yellow-orange in color. After 0.5 h, a pale yellow solid separated from solution. After 19 h, the solid was collected by filtration, it was washed with ethanol, and dried in vacuo to give a pale yellow solid (0.277 g, 86.3% yield), mp 203° C.

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