Dimethylformamide → HCID 22909643, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring heterogeneous mixture of 5-(2-pyridyl)-1,3,4-oxadiazole-2-thiol potassium salt (2.17 g, 0.19 mol) in DMF (25 ml) under an N2 atmosphere, was added 2.85 g (0.01 mol) of 4-bromo-2,6-ditertbutylphenol. The mixture was stirred for 24 h at 110° C. After cooling, the slurry was diluted with water (100 ml) and extracted with Et2O (4×35 ml). The Et2O extracts were combined and washed with water (2×50 ml) and saturated NaCl solution (50 ml) and then dried (MgSO4). The solvent was removed in vacuo to give a solid. Chromatography on silica gel using 1/4 ethyl acetate/hexanes gave 2-(2,6-ditertbutyl-4-hydroxyphenyl)thio-5-(2-pyridyl)-1,3,4-oxadiazole (45) as a white solid (1.5 g, 40% yield; mp 128°-129° C.).

Provenance & Evidence