Dimethyl Sulfoxide → HCID 59749538, compound

Participants

Reaction Steps

A Swern-type reagent was formed in standard fashion: oxalyl chloride (9.15 mL as a 2M soln. in CH2Cl2) in CH2Cl2 (23 mL) was cooled to −78° C. and treated with a solution of DMSO (2.85 mL, 36.8 mmol) in CH2Cl2 (23 mL) for 30 m. To this solution was added 5-{1-[2-(4-methoxy-benzylsulfanyl)-4,5-dihydro-3H-imidazol-4-yl]-ethyl}-quinoline (Intermediate E5) (4.7 g, 12.4 mmol) in CH2Cl2 (30 mL) and stirring continued for 45 m at −78° C. Triethylamine (9 mL) was added at −78° C. and warmed to rt for 40 m. The reaction mixture was diluted with brine and CH2Cl2. The aqueous layer was extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and evaporated to dryness. Chromatography on SiO2 with 80 to 100% ethyl acetate:hexanes yielded 5-{1-[2-(4-methoxy-benzylsulfanyl)-3H-imidazol-4-yl]-ethyl}-quinoline (Intermediate E6) 3.45 g (74%).

Provenance & Evidence