2-Amino-4,5,6,7-tetrahydrobenzothiazole → N-[2-(1-cyclohexenyl)ethyl]-N'-[4,5,6,7-tetrahydrobenzothiazolyl]thiourea

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Reaction Steps

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (1.67 g, 10 mmol) and 2-amino-4,5,6,7-tetrahydrobenzothiazole (1.54 g, 10 mmol) in dimethylformamide (100 mL) was heated at 100° C. for 120 h. The reaction was cooled to room temperature, the solvent removed under reduced pressure, the residue taken up in ethyl acetate and washed with 1N HCl. The organic layer was concentrated and the residue recrystallized from ethyl acetate-hexanes to provide 426 mg (13 %) of the titled product: IR (KBr, cm-1) 3169, 3031, 2931, 1580, 1258, 1198; 1H NMR (300 MHz, DMSO-d6) δ 11.41 (br s, 1H), 10.05 (br s, 1H), 5.43 (s, 1H), 3.58 (m, 2H), 2.6-1.9 (m, 10H), 1.7 (m, 4H), 1.5 (m, 4H); MS (FD) m/e 321 (M+); UV (EtOH) 298 nm (ε-12157), 257 nm (ε=6569), 201 nm (ε=12172). Anal. Calcd for C16H23N3S2 : C, 59.97 H, 7.21; N, 13.07. Found: C, 60.06; H, 6.95; N, 12.82.

Provenance & Evidence