Triethylamine → 3-(2,6-Dimethylphenyl)-1-isopropyl-2-thioxo-imidazolidin-4-one

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Reaction Steps

A mixture of the crude N-isopropyl glycine (21.2 g), 2,6-dimethylphenyl-isothiocyanate (16.3 g), triethyl amine (21.0 g) and chloroform (300 mL) was heated at reflux for 4 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with 2N HCl (2×300 mL), then with water. The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Crystallization from ethanol afforded the title compound (12.9 g) as a white solid, m.p. 135°-137° C. Anal. Calcd. for. C14H18N2OS: C, 64.09; H, 6.92; N, 10.68. Found: C, 63.99; H, 6.72; N, 10.67. Mass spectrum (+FAB, [M+H]+) m/z 263.

Provenance & Evidence