Dimethyl Sulfoxide → HCID 21472503, compound

Participants

Reaction Steps

Cool a solution of oxalyl chloride (1.43 mL) in CH2Cl2 (30 mL) to -78° C., add DMSO (2.32 mL) dropwise over 15 mins., stir for 15 min., then add a CH2Cl2 (20 mL) solution of the product of Step 5 (1.3 g) over 20 min. Stir the mixture for 30 min, treat with Et3N (9.2 mL) and stir for an additional 30 min. at -78° C., followed by 1.5 h at room temperature. Quench the reaction mixture with water and dilute with CH2Cl2 (100 mL). Separate the organic fraction, wash sequentially with 1N HCl (1×50 mL), sat. NaHCO3 (1×50 mL) and brine (1×50 mL), dry over MgSO4, filter and concentrate under reduced pressure to yield an oil. Chromatograph on silica gel, eluting with 50-100% EtOAc/hexane to give 3,4-dichloro-β-(2-oxoethyl)-N-methyl-N-[(2-methoxyphenyl)methyl] benzenepropanamide (950 mg).

Provenance & Evidence