Dimethyl Sulfoxide → 1-[3-(4-Cyanophenyl)propyl]-3,3-dimethyl-1-(2-oxoethyl)urea

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (4.84 g, 0.038 mol) was added dropwise to a stirred solution of DMSO (5.9 g, 0.0763 mol) and dichloromethane (100 mL) at −78° C. After 15 min at the same temperature, 1-[3-(4-cyanophenyl)propyl]-1-(2-hydroxyethyl)-3,3-dimethylurea (7 g, 0.0254 mol) in dichloromethane was added and stirring continued for 3 h under a nitrogen atmosphere. Triethylamine (12.8 g, 0.127 mol) was added (dropwise), and the reaction mixture was then warmed slowly to −30° C. The reaction mixture was quenched with 10% citric acid (aq.) and extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated to yield 6.5 g of the crude title compound, which was used without further purification.

Provenance & Evidence