Methanesulfonyl chloride → HCID 18789928, compound

Participants

Reaction Conditions

Reaction Steps

A portion (510 mg, 1.32 mmol) of the 1-(2-acetamido-4-aminophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (4) above was dissolved in pyridine (5 ml) and, thereafter, the solution was cooled to 0° C. and methanesulfonyl chloride (0.21 ml, 2.63 mmol) was added, followed by stirring at room temperature for 2 h. Thereafter, the solvent was evaporated from the reaction mixture and the resulting residue was diluted with an aqueous solution of sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried with sodium sulfate and the solvent was evaporated, with the resulting residue being purified by being subjected to column chromatography on silica gel using, as an eluent, chloroform containing methanol (6%). The resulting product was dissolved in methanol (10 ml) and the HCl as generated by adding conc. sulfuric acid to ammonium chloride was passed through the resulting solution. Thereafter, the solvent was evaporated for drying to yield the titled compound 1-(2-acetamido-4-methanesulfonamidophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (420 mg) as a foamy substance of ivory color.

Provenance & Evidence