Acetonitrile → (NZ)-N-[5-methylidene-3-(2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl)-1,3-thiazolidin-2-ylidene]imidazole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

The crude imine (Example 22C, 169 mg, <0.52 mmol) was dissolved into acetonitrile (10 mL), treated with diisopropylethylamine (130 μL, 0.75 mmol) and carbonyl diimidazole (94 mg, 0.58 mmol), and then heated near 80° C. overnight. The mixture was concentrated and chromatographed through silica (Oct. 40, 1950 to 25/25/50% EtOAc/CH2Cl2/hexanes) to give the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 4.83 (2 H), 5.42 (1 H), 5.45 (1 H), 7.01 (1 H), 7.26-7.35 (3 H), 7.44 (1 H), 8.10 (1 H); MS (ESI) m/z 415 (M+H)+.

Provenance & Evidence