Aniline → N-[5-(3-Bromo-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

Participants

Reaction Conditions

Reaction Steps

N-[5-(4-amino-3-bromo-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 7a) (1.0 g, 3.07 mmol) is converted into the corresponding sulfonyl chloride by the procedure described for the conversion of aniline (Example 1a) to sulfonyl chloride (Example 3a). A sample of this crude sulfonyl chloride (1.0 g, 2.4 mmol) is dissolved in dioxane (5 ml) and the resulting solution is added to a stirred solution of sodium sulfite (0.615 g, 4.9 mmol) and sodium hydrogen carbonate (0.41 g, 4.9 mmol) in water (5 ml) at 75° C. After 1 hour at 75° C. bromoacetic acid (0.679 g, 4.9 mmol) is added. The reaction is stirred for an additional 6 hours at 75° C. When cool the mixture is diluted with water (200 ml) and extracted with dichloromethane (3×100 ml). The combined organic extracts are washed with brine (100 ml, dried (MgSO4) and the solvent removed. Purification by chromatography on silica (EtOAc) affords the title compound.

Provenance & Evidence