Water → N'-(3-Iodobenzoyl)-3-methoxybenzohydrazide

Participants

Reaction Steps

To a solution of 3-iodobenzohydrazide (10.0 g, 38.16 mmol) in dry THF/DMF (100.0 ml:10.0 ml) was slowly added 3-methoxybenzoyl chloride (7.0 g, 42.03 mmol) at 0° C. under nitrogen. During addition of 3-methoxybenzoyl chloride, white solid was appeared. After addition of 3-methoxybenzoyl chloride, the reaction was allowed to warm up to room temperature. The reaction mixture was stirred for 19 hours at room temperature and then pyridine (20.0 ml) was added and stirred for additional 45 min. Water (300.0 ml) was added to reaction mixture. The white solid was obtained and collected by filtration and washed with water. After dried under vacuum, product was obtained as white powder in 12.4 g (82.0%). 1H NMR (400 MHz, DMSO-d6, δ): 10.62 (s, 1H, NH), 10.56 (s, 1H, NH), 8.25 (t, J=1.6 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 3.81 (s, 3H, OCH3).

Provenance & Evidence