Dimethylformamide → 2-benzyl-N-ethyl-4-methoxybenzamide

Participants

Reaction Steps

To a 0 C solution of 2-benzyl-4-methoxybenzoic acid (5 g) in 250 mL CH2Cl2 were added a catalytic amount of DMF and a solution of oxalyl chloride (2 mL) in 40 mL CH2Cl2. The reaction was warmed to room temp and stirred overnight, then concentrated to dryness and azeotroped from toluene (2×). The residue was dissolved in 50 mL THF and added dropwise to a 0 C solution of ethylamine (10 mL, 70% aqueous solution) in 200 mL THF. The reaction was warmed to room temp and stirred for 2 h, then quenched with saturated aqueous KHSO4 solution and extracted with EtOAc (2×). The organic solutions were dried (Na2SO4) and concentrated, then triturated with hexanes to give 5.2 g of 2-benzyl-N-ethyl-4-methoxybenzamide.

Provenance & Evidence