Benzoic Acid → HCID 178504832, compound

Participants

Reaction Steps

To a suspension of 6-benzyl-4-methylsulfanyl-2,6,7,8-tetrahydro-1,2,3,5,6-pentaazaacenaphthylene (2.08 g, 7.00 mmol) in anhydrous dichloromethane (100 ml) was added solid m-CPBA (4.69 g, 77% pure, 21.0 mmol) directly. The reaction became clear immediately. After stirring overnight at room temperature, a white precipitate crashed out (benzoic acid and product) from the reaction. The reaction was monitored by HPLC to ensure completion (>95%). It was noreworthy that extended reaction time led to over-oxidation and 12-15 hours seemed optimal in most cases. DMSO (50-70 ml) was added to quench the reaction and the reaction was stirred for 30 min at room temperature. aq. NaHCO3 (100 ml) was added in one shot while stirring. Some precipitates remained. The off-white precipitates were filtered washed with a lot of water to give the desired product. The dichloromethane layer was separated, washed with aq. NaCl twice and concentrated. More precipitate crashed out. The precipitates were filtered and washed with a lot of water to give the desired product as an off-white solid. Combining all products yield product in total (1.35 g, 58%). The product was further dried by high vacuum pump and was used without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 13.64 (s, 1H), 7.28-7.41 (m, 5H), 4.89 (s, 2H), 3.74 (t, J=6.4 Hz, 2H), 3.15 (t, J=6.4 Hz, 2H), 2.51 (s, 3H). LC-Mass (m/e): 330.54 (M+1).

Provenance & Evidence