1,4-Dioxane → 5-Bromo-4-chloro-N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round-bottomed flask was added 2,5-dibromo-4-chlorothiazole (5.9 g, 21 mmol), p-dioxane (50 mL, 587 mmol), and 4-methoxybenzylamine (3 mL, 21 mmol). The solution was stirred at 75° C. for 4 hours. The reaction was cooled to room temperature, and the solvent was removed. The residue was dissolved in EtOAc and washed with saturated NaHCO3 (1×25 mL), saturated sodium chloride (1×25 mL), water (1×25 mL), and dried over Na2SO4, filtered and concentrated in vacuum. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient (5%→50% EtOAc in hexane) to provide N-(4-methoxybenzyl)-5-bromo-4-chlorothiazol-2-amine (5.5 g, 80% yield), m/z (%): 334.1 (100%, M++H).

Provenance & Evidence