Methyl N-(triethylammoniosulfonyl)carbamate → 2-(Chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole

Participants

Reaction Steps

N′-(Chloroacetyl)-3-(methyloxy)-4-nitrobenzohydrazide (1.00 g, 3.48 mmol) and Burgess' reagent (0.994 g, 4.17 mmol) in THF (15 mL) was heated to 120° C. for 20 minutes in the microwave. The reaction was complete by TLC. Purification by flash chromatography provided the title compound (0.802 g, 2.93 mmol, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.04 (s, 3H), 5.16 (s, 2H), 7.72 (dd, J=8.4, 1.8 Hz, 1H), 7.84 (d, J=1.8 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H).

Provenance & Evidence