Triethylamine → N-(2-amino-4-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide

Participants

Reaction Steps

A solution of 3-iodo-4-methylbenzoic acid (0.26 g, 1 mmol) in SOCl2 (5 mL) was refluxed for 2 h, and then evaporated in vacuo to remove excess SOCl2. The residue was dissolved in 5 mL anhydrous THF and added to a solution of triethylamine (0.12 g, 1.2 mmol), 2-amino-4-(4-methyl-1H-imidazol-1-yl)aniline (0.18 g, 1 mmol) and DMAP (24 mg) in 5 mL anhydrous THF in dropwise. The result mixture was stirred at rt for 20 hrs, and evaporated in vacuo. The residue was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3) to give 0.16 g product as a pale yellow solid (37.0%). LC/MS: m/z [M+H]+ 433.0520.

Provenance & Evidence