Triethylamine → 4-Imidazolidinone, 1-ethyl-3-(2-phenylethyl)-2-thioxo-

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Reaction Steps

A mixture of the crude N-ethyl glycine (18.4 g), phenethyl-isothiocyanate (16.3 g), triethyl amine (20.2 g) and chloroform (300 mL) was heated at reflux for 18 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with 1N HCl (2×300 mL), then evaporated to dryness. Purification was achieved by flash chromatography on silica gel (20% ethyl acetate in hexane) The title compound (15.0 g) was obtained as an off-white solid, m.p. 66°-68° C. Anal. Calcd. for. C13H16N2 O S: C, 62.87; H, 6.49; N, 11.28. Found: C, 63.03; H, 6.49; N, 11.32. Mass spectrum (EI, M.+) m/z 248.

Provenance & Evidence