Dimethyl Sulfoxide → HCID 19077438, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.11 ml, 1.30 mmol) in dichloromethane (8 ml) at -78° C. was added dimethylsulfoxide (0.20 ml, 2.60 mmol) and over a 5 minute period l-(1 -hydroxydodecyl)-3,7-dimethylxanthine (0.40 g, 1.10 mmol) in dichloromethane (4 ml). The reaction was stirred at -78° C. for 30 minutes and after the addition of triethylamine (0.72 ml, 5.20 mmol), the reaction was allowed to warm to 25° C. over 30 minutes. Water (10 ml) was added, the organic phase separated and the aqueous phase washed with dichloromethane (10 ml). The organic portions were combined and dried with magnesium sulfate, and the solvent evaporated to give a slightly yellow solid. The crude yellow solid was recrystallized from hot hexane to obtain 0.32 g of a white solid, 1-(1-oxododecyl)-3,7-dimethylxanthine (80% yield).

Provenance & Evidence