Sodium Bicarbonate → N-[5-[[(4,5-dimethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide

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Reaction Steps

N-[5-(Acetylthio)-2-thiazolyl]acetamide (0.050 g, 0.23 mmol) was dissolved in dry THF (10 ml) and here potassiumtert-butoxide (1.0 M solution in THF, 0.25 ml, 0.25 mmol) was added to the mixture. The reaction mixture was stirred at rt for 15 min., and 2-(bromomethyl)-4,5-dimethyloxazole (0.064 g, 0.34 mmol) was added to this mixture. The reaction mixture was stirred at rt for 3 h and saturated aqueous NaHCO3 solution (20 mL) was added to the mixture. The organic layer was separated and the aqueous layer was extracted with dichloromethane (1×20 mL). The combined organic layers was concentrated. The residue was purified by flash column chromatography (SiO2; methanol:dichloromethane/1:20) to afford N-[5-[[(4,5-dimethyl-2-oxazolyl)methyl]thio]-2-thiazolyl] acetamide (15 mg, 23%) as a yellow solid. 1H NMR (CDCl3) δ 11.78 (s, 1H), 7.38 (s, 1H), 3.90 (s, 2H), 2.30 (s, 3H), 2.22 (s 3H), 2.05 (s, 3H); MS m/e 284 (M+H)+;

Provenance & Evidence