Chlorosulfonic acid → 5-(2-Acetylamino-4-methyl-thiazol-5-yl)-2-methoxy-benzenesulfonyl chloride

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Reaction Steps

To N-[5-(4-Methoxy-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 28a) (0.0947 g, 0.361 mmol) is added at 0° C. chlorosulfonic acid (3 ml) followed by dichloromethane (1 ml). The reaction mixture is stirred below 0° C. for 2 hours then poured into crushed ice and extracted with dichloromethane (3×5 ml). The organic layers are combined and dried over MgSO4. The solvent is removed to give 5-(2-acetylamino-4-methyl-thiazol-5-yl)-2-methoxy-benzenesulfonyl chloride, which is dissolved into dioxane (2 ml). To this solution is added N,N-dimethyl-ethylenediamine (0.0636 g, 0.72 mmol) and 2M Na2CO3 (0.5 ml). The reaction mixture is stirred at room temperature for 2 hours. The mixture is concentrated and the residue is taken into water (2 ml) and extracted with dichloromethane (3×5 ml). The combined organic layers are dried over MgSO4. After filtration the solvent is removed in vacuo to give the titled compound which is dried overnight in vacuum oven at 25° C. MH+ (ESMS): Mp 413.0° C.

Provenance & Evidence