Iodoethane → 3-(2,6-Dimethylphenyl)-2-ethylsulfanyl-3,5-dihydro-imidazol-4-one

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Reaction Steps

The title compound was prepared by the procedure described in Example 12 using 8.0 g of 2-[3-(2,6-dimethylphenyl)-thioureido]-acetamide, 25.0 g of ethyl iodide, and (200 mL) ethanol. Crystallization from hexane/diethyl ether mixture afforded the title compound as a light yellow solid (2.4 g), m.p. 86°-88° C. Anal. Calcd. for. C12H16N2O S: C, 62.87; H, 6.49; N, 11.28. Found: C, 62.98; H, 6.57; N, 11.30. Mass spectrum (El, M.+) m/z 248. 1H-NMR (DMS-d6 ; 400 MHz) δ7.27-7.30 (m, 1 H), 7.21 (m, 1 H), 7.19 (m, 1 H), 7.33 (d, 1 H), 4.42 (s, 2 H), 3.06 (q, 2 H), 2.07 (s, 6H), and 1.26 ppm (t, 3 H).

Provenance & Evidence