Water → N-(4-{2-[4-(azidomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Participants

Reaction Steps

To a solution of N-(4-{2-[4-(chloromethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (203.3 mg, 0.650 mmol) in anhydrous N,N-dimethylformamide (2 ml) was added sodium azide (233.7 mg, 3.595 mmol), and the mixture was stirred at room temperature for 3.5 hr. Water (20 ml) and ethyl acetate (20 ml) were added to the reaction mixture, and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diisopropyl ether (10 ml) was added to the residue, and the mixture was filtered and dried under reduced pressure to give N-(4-{2-[4-(azidomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (160.5 mg, 0.503 mmol, yield 77.3%) as a white solid.

Provenance & Evidence