Diisopropylethylamine → 5-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-[1,2,4]oxadiazole

Participants

Reaction Steps

2-Furan-2-yl-3-methyl-3,5-dihydro-imidazol-4-one (described in Takeuchi, H., Hagiwara, S., Eguchi, S., Tetrahedron (1989) 6375-6386) (50 mg, 0.30 mmol) was dissolved in dioxane (3 ml) and Lawesson reagent (136 mg, 0.34 mmol) was added. The reaction mixture was heated to reflux over night and then allowed to room temperature at which time DIPEA (212 ml, 1.22 mmol) and 3-chloromethyl-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (140 mg, 0.61 mmol) was added. The resulting mixture was heated to reflux for 5 h and then kept at room temperature over night. Ethyl acetate was added and the reaction mixture was washed with water followed by brine. The organic phase was dried over MgSO4 and evaporated. The title compound (13 mg, 11%) was obtained by flash chromatography using 1% methanol in chloroform. 1H NMR (CD3OD) d (ppm): 7.96 (m, 1H), 7.90 (m, 1H), 7.60 (dd, 1H), 7.57 (ddd, 1H), 7.46 (t, 1H), 7.09 (s, 1H), 6.86 (dd, 1H), 6.52 (dd, 1H), 3.95 (s, 2H), 3.74 (s, 3H).

Provenance & Evidence