Toluene → 1-(4-Aminobenzoyl)azepan-2-one

Participants

Reaction Steps

Into a 3000 mL three-neck reactor were charged caprolactam (150 g, 0.703 mol), toluene (1300 mL), and pyridine (680 mL); the reactor was then purged with nitrogen. Under ice bath, p-sulfinylaminobenzoyl chloride (147.1 g, 0.730 mol) was added with stirring to the above mixture. After removing the ice-bath, the reaction mixture was stirred at room temperature for 14 hours. After this, pyridine chloride was removed by filtration and the filtrate was washed with 5% sodium bicarbonate solution two times, and then concentrated to remove the solvent. The residue was recrystallized from ethyl acetate to give N-(p-aminobenzoyl)caprolactam, a polymerizable lactam monomer.

Provenance & Evidence