3,5-diiodo-N'-(3-methoxybenzoyl)benzohydrazide → 2-(3,5-Diiodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Participants

Reaction Steps

3,5-Diiodo-N′-(3-methoxybenzoyl)benzohydrazide (5.0 g, 9.58 mmol) was suspended in POCl3 (50.0 ml) and heating was started. During heating white solid of starting materials dissolved into a clear solution (130° C.). The reaction was kept at 100° C. and the reaction was monitor by thin layer chromatography. After 5 h, the reaction mixture was brought to room temperature and was carefully dropped into ice-water (1000.0 ml). White solid precipitated out was collected by filtration and washed with water. After dried, the crude product was purified by silica gel column chromatography eluting with dichloromethane and ethyl acetate in 9.5:0.5 ratio. After evaporating solvent the white solid was recrystallized from acetone/water and finally dried under vacuum. Pure product was obtained as white solid in 3.4 g (70.8%) yield. 1H NMR (400 MHz, CDCl3, δ): 8.43 (dd, J1=1.6 Hz, J2=0.8 Hz, 2H), 8.23 (t, J=1.6 Hz, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.66 (m, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.12 (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 3.92 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 165.06, 161.67, 159.98, 148.05, 134.63, 130.31, 126.95, 124.44, 119.44, 118.56, 111.66, 94.98, 55.59.

Provenance & Evidence