Chloride → 2-nitro-N-isopropyl-5-phenoxybenzamide

Participants

Reaction Conditions

Reaction Steps

A solution of 34A (1.0 g, 3.86 mmol) in CH2Cl2 (15 mL) was treated with one drop of DMF. Oxaly chloride (2.2 mL, 2M in CH2Cl2, 4.4 mmol) was added dropwise at room temperature. The reaction mixture was stirred for 1 hour, and then concentrated to dryness. The crude acid chloride was dissolved in CH2Cl2 and cooled to 0° C. Diisopropylamine (600 mg, 10 mmol) in CH2Cl2 (2 mL) was added slowly and the resulting mixture was stirred for one hour at room temperature. The reaction was concentrated and partitioned between EtOAc (20 mL) and 1M HCl (20 mL). The organic layer was washed with 1 M HCl (20 mL), saturated aqueous NaHCO3 (20 mL), and brine (20 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to a brown solid. The crude amide was recrystallized from EtOAc/heptane to afford 34B (740 mg, 64%).

Provenance & Evidence