N-Ethylaniline → N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (12 ml, 17.3 g, 0.14 mol) was added dropwise to a solution of 2-iodo-4-nitrobenzoic acid I-1 b (20 g, 68.3 mmol) in dichloromethane (137 ml). N,N-Dimethylformamide (0.1 ml) was added to the reaction mixture via syringe, the reaction mixture was stirred at 23° C. for 1 hour, and another portion of N,N-dimethylformamide (0.1 ml) was added. After stirring the reaction mixture another 2 hours, the reaction mixture was concentrated in vacuo. The residue was taken up in dichloromethane (137 ml), and DMAP (50 mg) and triethylamine (14.3 ml, 10.3 g, 0.102 mol) were added. The mixture was cooled to 0° C. and N-ethylaniline (10.1 ml, 9.9 g, 82 mmol) was added over a 10 min period. The reaction mixture was warmed to 23° C. After 16 hours at this temperature, water (150 ml) was added, and the layers were separated. The organics were washed with 1 N HCl (2 100-ml portions), dried over anhydrous sodium sulfate, and were concentrated. Purification of the residue by flash column chromatography (dichloromethane) afforded N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide I-1c (24.3 g, 93%).

Provenance & Evidence