Benzoyl chloride → N-Allylbenzamide

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask with a stir bar, a solution of allyl amine (10 mL, 133.6 mmol) in dichloromethane (350 mL) was cooled to 0° C. A solution of benzoyl chloride (17.05 mL, 147.0 mmol) in dichloromethane (20 mL) was added dropwise via addition funnel. Once the addition was complete, the solution was stirred at 0° C. for 2 h. The solution was concentrated and the residue was purified on silica gel chromatography (Combiflash. Rf system, 330 g RediSep cartridge) using EtOAc/hexanes as a mobile phase. The desired fractions were collected and concentrated to afford N-allylbenzamide (19.6 g, 91%) as a yellow oil. N-allylbenzamide (1.0 g, 6.21 mmol) was dissolved in dichloromethane (60 mL) and cooled to −78° C. A Tygon tube connected to an ozone generator was fitted with a gas dispersion tube and a stream of ozone was bubbled through the solution at −78° C. Once a pale blue color persisted in the solution, the ozone stream was removed and the solution was treated with dimethyl sulfide (13 mL, 186 mmol) and allowed to warm to ambient temperature over 30 min. The solution was concentrated to give a yellow residue that was subjected to high vacuum for 2 h. The resulting N-(2-oxoethyl)benzamide was used without further purification.

Provenance & Evidence