Dimethyl Sulfoxide → HCID 21472504, compound

Participants

Reaction Steps

Oxalyl chloride (7.74 g) in CH2Cl2 (80 mL) was added to a -78° C. solution of DMSO (9.5 g) in CH2Cl2 (30 mL) over 15 mins. This mixture was stirred for 15 minutes whereupon a CH2Cl2 (50 mL) solution of 3,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-phenylbenzenepropanamide (17.15 g) was added over 20 minutes. The mixture was stirred for 30 minutes and then treated with a solution of Et3N (14.76 g) in CH2Cl2 (20 mL) and stirred for an additional 30 minutes at -78° C., followed by 1.5 hours at room temperature. The reaction mixture was washed with water (100 mL), the organic fraction separated, dried over MgSO4, filtered and concentrated under reduced pressure to yield an oil (20 g). Silica gel chromatography eluting with 5-15% EtOAc/Hex gave the title compound (15.2 g).

Provenance & Evidence