Hydrochloric Acid → HCID 14719514, compound

Participants

Reaction Conditions

Reaction Steps

In the meantime, 3.36 g of 4-methoxysalicylic acid was dispersed in 30 ml of methylene chloride under argon atmosphere, and the dispersion was cooled to -15° C. To the dispersion were added 4.47 g of triethylamine and 4.58 g of ethyl chlorocarbonate, and the mixture was agitated for 1.5 hours. To the mixture was added the 2-aminoethyl-n-octylsulfide which had been dissolved in 10 ml of methylene chloride, and the mixture was agitated at -15° C. for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 6.37 g of 2-(2'-ethoxycarbonyloxy-4'-methoxybenzoylamino)ethyl-n-octylsulfide, which was dissolved in 100 ml of methanol. To the solution was added 23 ml of 1N aqueous solution of sodium hydroxide, and the mixture was agitated for 35 minutes. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 3.55 g of 2-(2'-hydroxy-4'-methoxybenzoylamino)ethyl-n-octylsulfide.

Provenance & Evidence