1-(2-Isothiocyanatoethyl)cyclohex-1-ene → N-(2-[1-cyclohexenyl]ethyl)-N'-[(4-isopropyl)pyridinyl]thiourea

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Reaction Steps

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (0.36 g, 2.2 mmol) and 2-amino-4-isopropylpyridine (0.36 g, 2.2 mmol) in N,N-dimethylformamide (20 mL) was heated at 100° C. for 96 h. The reaction was cooled to room temperature, solvents removed under reduced pressure, taken up in ethyl acetate, washed with 1N aqueous HCl. The organic layer was concentrated and the residue purified by HPLC (elution with hexanes-EtOAc) to afford 169 mg (5.6%) of the titled product: mp 105°-106° C.; IR (KBr, cm-1) 3215, 2931, 1614 1556, 1534, 1487, 1199; 1H NMR (300 MHz, DMSO-d6) δ 11.65 (t, 1H), 10.40 (S, 1H), 8.30 (d, 1H), 7.20 (S, 1H), 6.93 (d, 1H), 5.52 (s, 1H), 3.63 (q, 2H), 2.80 (m, 1H), 2.22 (t, 2H), 1.95 (m, 4H), 1.62-1.42 (m, 4H), 1.18 (d, 6H); MS (FD) m/e 303 (M+); UV (EtOH) 290 nm (ε=17565), 266 nm (ε=18863), 247 nm (ε=15125), 203 nm (ε=23091). Anal. Calcd for C17H25N3S: C, 67.28;H, 8.30; N, 13.85. Found: C, 67.55; H, 8.48; N, 13.94.

Provenance & Evidence