Dimethyl Sulfoxide → 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a dichloromethane (50 mL) solution of oxalyl chloride (1.47 mL, 16.8 mmol) at −78° C. was added methyl sulfoxide (1.47 mL, 20.5 mmol). After 15 minutes 1-Cyclobutyl-5-hydroxymethyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (2.21 g, 10.0 mmol, in 20 mL dichloromethane) was added. After 20 minutes triethylamine (4.26 mL, 20.6 mmol) was added and the reaction was allowed to warm to 23° C. Upon dilution with saturated sodium bicarbonate and dichloromethane the product was extracted into dichloromethane. The organic layer was dried over sodium sulfate and concentrated to give 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde (2.17 g).

Provenance & Evidence