Acetic Acid → 4-Acetamido-3-iodobenzaldehyde thiosemicarbazone

Participants

Reaction Steps

A solution of 0.728 g (0.008 mole) of thiosemicarbazide (Aldrich T3,340-5) in 25 mL of water containing 1.6 mL of glacial acetic acid was added to a solution of 2.319 (0.008 mole) of 4-acetamido-3-iodobenzaldehyde (33) in 40 mL of absolute ethanol (heating was required to make this dissolve) at 80°. The mixture was stirred at this temperature for 45 minutes. A white precipitate developed in the solution which was filtered after cooling the reaction mixture to give 2.55 (88%) of 34 as white crystals, mp 241-43° (dec.). Infrared (IR) and NMR analysis gave the following results:

Provenance & Evidence