Sodium hydride → HCID 178467941, compound

Participants

Reaction Conditions

Reaction Steps

Under N2, NaH (60% oil dispersion, 1 g, 0.025 mol) was added to DMF (20 ml) and heated at 70° C. while a solution of 2-(4-hydroxyphenyl)-4-(2-thienyl)imidazole (5.0 g, 0.021 mol) in DMF (40 ml) was added dropwise. After heating at 70° C. for 0.5 hours, a solution of the tosylate of 2 (0.022 mol) in DMF (25 ml) was added dropwise and the mixture heated at 110° C. After 18 hours, the reaction mixture was poured into H2O and the suspension extracted with EtOAc (4X). The organic extracts were washed with H2O, saturated NaCl, dried, filtered and concentrated to dryness. The residue was treated with AcOH (25 ml) and H2O (175 ml) and the mixture stirred at room temperature. After 18 hours, the aqueous layer was extracted with Et2O (2X), adjusted to ph>10 with saturated Na2CO3 and extracted with CHCl3 (3X). The CHCl3 extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel eluting with 5% CH3OH--CHCl3 saturated with NH3 to yield 0.56 g (6.6%) of 3; m.p. 144°-6° C. (CH3CN).

Provenance & Evidence