Potassium Iodide → 4-iodo-N,3,5-trimethylbenzamide

Participants

Reaction Conditions

Reaction Steps

4-Amino-3,5,N-trimethyl-benzamide (850 mg, 4.77 mmol) is suspended in hydrochloric acid (37%, 2 mL), stirred until completely dissolved then cooled to 0° C. Sodium nitrite (494 mg, 7.15 mmol) in water (0.5 mL) is added and the mixture stirred for 1 hour at 0° C. Potassium iodide (2.38 g, 14.31 mmol) in 1.5 mL water is added and the mixture stirred for 15 minutes. The mixture is diluted with dichloromethane then washed with 10% aqueous sodium thosulfate solution, dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound. (Yield 850 mg).

Provenance & Evidence