Hydrochloric Acid → HCID 53950580, compound

Participants

Reaction Steps

A solution of the compound obtained in step A (3 g, 8.7 mmoles) in chloroform (50 ml), was added with thionyl chloride (1.2 ml, 17.4 mmoles) and 3 drops of pyridine. The reaction mixture was refluxed for 5 hours, then evaporated to dryness. The residue was redissolved in chloroform and re-evaporated to dryness three times. The resulting 4-[2-(adamant-1-yl)ethoxycarbamoyl]benzoyl chloride was dissolved in THF (50 ml) and the solution was added slowly to a solution of hydroxylamine hydrochloride (0.7 g, 10.4 mmoles) and sodium bicarbonate (0,7 g, 8.7 mmoles) in 1N sodium hydroxide (10.4 ml, 10.4 mmoles) and THF (20 ml), then stirred at room temperature for 8 hours, acidified with 1N HCl, and THF was evaporated in the cold. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over anhydrous sodium sulfate and the solvent was evaporated off. The resulting crude was treated with warm ethyl ether and filtered to give 1.5 g of the title compound (48% yield); m.p.=198-200° C.

Provenance & Evidence