Triethylamine → (S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (4.5 ml) in dichloromethane (100 mL) at −78° C., dimethylsulfoxide (7.4 mL) in dichlororomethane (40 mL) was added. After the addition was complete, the solution was stirred for another 30 minutes at −78° C. A solution of (S)—N-[2-(3,4-dichloro-phenyl)-4-hydroxy-butyl]-N-methyl-benzamide (14.6 g) in dichloromethane (35 mL) and dimethylsulfoxide (7 ml) was then added drop wise. The solution was stirred at −78° C. for one hour. Triethylamine (29 mL) was added drop wise to the reaction and after 20 minutes the ice bath was removed and the solution was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with dichloromethane (200 mL), and washed with dilute aqueous hydrochloric acid (150 mL), water (150 mL), and aqueous sodium bicarbonate (150 mL). The separated organic layer was dried and evaporated then dissolved in ether. The white precipitate that formed, was filtered and dried giving the title compound (9.1 g). Rf=0.41 methylene chloride:methanol (95:5).

Provenance & Evidence