Nitric Acid → 2-(p-Nitrobenzyl)-4-(4-pyridyl)thiazole

Participants

Reaction Conditions

Reaction Steps

A solution of 2-benzyl-4-(4-pyridyl)thiazole (4.50 g, 0.018 mol) in chloroform (25 mL) was added dropwise to concentrated sulfuric acid (15 mL). The resulting mixture was cooled to 10° C. and fuming nitric acid (1.45 g, 0.97 mL) carefully added dropwise such that the reaction temperature did not exceed 40° C. The mixture was allowed to stir for thirty minutes, carefully neutralized with saturated sodium carbonate and the layers separated. The aqueous layer was reextracted with chloroform (2×25 mL) and the combined organic extracts were washed with brine (20 mL), dried over magnesium sulfate, and concentrated to afford a crude product (4.6 g). Several recrystallizations from hexane/ethyl acetate afforded pure 2-(p-nitrobenzyl)-4-(4-pyridyl)thiazole. mp. 140°-142° C.

Provenance & Evidence