Dimethyl Sulfoxide → HCID 57501304, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.26 mL, 3.0 mmol) in dichloromethane (10 mL) at −70° C. was added a solution of dimethyl sulfoxide (DMSO, 0.426 mL, 6.0 mmol) in dichloromethane (10 mL). After thirty minutes a solution of 4-(2-hydroxyethyl)-6-methoxy-2H-1,4-benzoxazin-3(4H)-one (Intermediate 126, 550 mg, 2.5 mmol) in dichloromethane (3.5 mL) was added dropwise and it was stirred for 90 minutes. Triethyl amine (1.74 ml, 12.5 mmol) was added it was stirred at −70° C. for another 45 minutes. The reaction was quenched with water and warmed to 0° C. It was diluted with dichloromethane, the aqueous phase was extracted with dichloromethane (3×25 mL) and the combined organic phases were washed with 1N HCl (2×25 mL), water (25 mL), 1M sodium carbonate solution (2×25 mL), water, brine, dried over magnesium sulfate and concentrated at reduced pressure. Chromatography on silica gel with dichloromethane/methanol (96:4) gave the product as a yellow oil, 292 mg (53%).

Provenance & Evidence