Dimethyl Sulfoxide → HCID 22010728, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (127 mg) in dichloromethane (20 ml) was added dimethyl sulfoxide (78 mg) at −78° C. and the solution was stirred at the same temperature for 10 minutes. A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(2-hydroxyethoxy)phenyl]benzamide (400 mg) in dichloromethane (5 ml) was added to the mixture at −78° C. After being stirred at −78° C. for 20 minutes, triethylamine (0.50 ml) was added to the mixture at the same temperature and the cooling bath was removed. The mixture was stirred at ambient temperature for 3 hours and the solution was washed successively with 1N hydrochloric acid, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(formylmethyloxy)phenyl]benzamide (399 mg) as an amorphous. To a mixture of the crude obtained aldehyde (399 mg) and hydroxylamine hydrochloride (174 mg) in ethanol (20 ml) was added potassium carbonate (173 mg) in water (2 ml) and the solution was stirred at ambient temperature for 2 hours. The mixture was diluted with ethyl acetate (30 ml) and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(2-hydroxyiminoethoxy)phenyl]benzamide (288 mg) as an amorphous.

Provenance & Evidence