Hydrochloric Acid → HCID 10487090, compound

Participants

Reaction Steps

To a solution of furan-3-carboxylic acid (26 g, 0.23 mol) in 250 mL of toluene was added 24.15 mL (0.276 mol) of oxalyl chloride and 1 drop of pyridine and the mixture was heated on a steam-bath for 2 h. The mixture was cooled to room temperature, and N,O-dimethylhydroxamine hydrochloride (24.66 g, 0.253 mol), 4-dimethylaminopyridine (DMAP, 1.2 g, 0.01 mol), and 600 mL of methylene chloride were added. The mixture was cooled to 0° C., 50.1 mL of pyridine in 50 mL of methylene chloride was added slowly, the mixture was heated to warm to room temperature (3 h), and 2 g of N,O-dimethyl-hydroxamine hydrochloride and 1 g of 4-dimethylaminopyridine (DMAP) were added. The resulting mixture was stirred for 12 h. The above mixture was cooled to 0° C., filtered, and the filtrate was washed with 3N HCl, brine, dried over sodium sulfate, and concentrated in vacuo to yield 14 g (39%) of 3-(N-methyl-N-methoxycarbamoyl)furan.

Provenance & Evidence