Ammonium Hydroxide → 3-iodo-4-methylbenzamide

Participants

Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.49 g, 28.6 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (3.90 g, 28.9 mmol) and 32% aqueous ammonium hydroxide solution (1.10 mL, 28.7 mmol) were sequentially added to a stirred solution of 3-iodo-4-methylbenzoic acid (5.00 g, 19.1 mmol) in N,N′-dimethylformamide (15 mL) at room temperature. After stirring overnight, the mixture was concentrated in vacuo and water and dichloromethane were added to the mixture. The organic layer was washed with 2N aqueous sodium hydroxide solution, brine, dried (MgSO4) and evaporated to give the title compound (4.34 g, 70%) as a yellow solid.

Provenance & Evidence