4-Toluenesulfonyl chloride → N-[2-(3-phenylsulfonyloxypropoxy)phenyl]acetamide

Participants

Reaction Steps

To a solution of N-[2-(3-hydroxypropoxy)phenyl]-acetamide (Example 113) (7.5 g, 36 mmol) in pyridine (90 ml), cooled to 0° C., was added p-toluenesulfonyl chloride (13.6 g, 56 mmol). After the tosyl chloride went into solution, the reaction was then allowed to stand at 5° C. for 16 hours. The reaction was poured onto ice, and a brown oil settled. The aqueous supernatant was decanted from the oil, and the residual oil taken up in diethyl ether. The diethyl ether was washed with cold (5C) 3N HCl and then with brine. The organic layer was dried (MgSO, and concentrated to afford a thick, brown oil, 5.3 g.

Provenance & Evidence