2-Mercapto-1-phenylethanone → HCID 86744603, compound

Participants

Reaction Steps

To a solution of 8.1 g (0.053 mol) of 2-mercapto-1-phenylethanone in 100 mL of toluene under nitrogen was added 10.2 g (0.053 mol) of 3-(4-methoxyphenyl)oxiranecarboxamide and the mixture was stirred and heated in an oil bath at 120o for 3 hrs. The solvent was removed under reduced pressure to give 18.1 g of crude product, which was dissolved in a minimum amount of a mixture of methylene chloride--ethyl acetate (8:2) and chromatographed using a Waters Prep. LC-system 500 A. Eluted with the same solvents and 200 mL fractions were collected. Fractions 18-21 provided 9.3 g of crude product of which was rechromatographed using ethyl acetate--hexane (75:25) as elutants. Fraction 7 after removal of the solvent yielded a residue, which after crystallization from ethyl acetate gave 0.9 g (5%) of rac.-(R,*R*)-α-hydroxy-4-methoxyphenyl-β-[ (2-oxo-2-phenylethyl)thio]benzenepropanamide, mp 132°-134°.

Provenance & Evidence