3-Chloropropionyl chloride → 1-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-chloro-propan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (0.530 g, 1.90 mmol) in 5 mL ethyl acetate was added 2 mL saturated aqueous sodium bicarbonate. The mixture was stirred rapidly and cooled to 0° C., and 3-chloro-propionyl chloride (0.219 mL, 2.30 mmol) was added dropwise over 2 minutes. Stirring was continued for 20 minutes, and 20 mL ethyl acetate was added to the reaction mixture. The organic phase was separated, dried over Na2SO4 and concentrated in vacuo to give 0.689 g (99%) of 1-(6-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-chloro-propan-1-one as an orange-white solid. MS: 367 (M+H)+.

Provenance & Evidence