Pentane → HCID 13784988, compound

Participants

Reaction Steps

Under a dry nitrogen atmosphere a mixture of 0.55 g (0.0035 mole) 2,6-difluorobenzamide, 0.48 g (0.0038 mole) oxalyl chloride, and 70 ml of toluene was heated at reflux for two hours. The mixture was cooled and distilled under reduced pressure to remove excess oxalyl chloride and approximately 60 ml of toluene. To the pot residue were added 30 ml of fresh toluene and 0.72 g (0.0035 mole) 5-amino-2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran dissolved in 30 ml of toluene. The resultant mixture was allowed to stir at room temperature for approximately 18 hours. Approximately 100 ml of n-pentane was added to this mixture. A white precipitate formed after stirring for an additional hour. This solid was collected by filtration to yield 0.74 g of N-[[(2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran-5-yl)amino]carbonyl]-2,6-difluorobenzamide (mp 183°-184.5° C.), Compound 1 of Table 1. The nmr and ir spectra were consistent with the proposed structure.

Provenance & Evidence