Sodium Hydroxide → HCID 44271328, compound

Participants

Reaction Steps

A solution of 0.161 g (0.41 mmol) of 2-(4-methylthiophenyl)-4-(3-nitrophenyl)-5-(4-pyridyl)-1H-imidazole [See Ex. 62 below] in 3.4 mL of HOAc-H2O (1:1) was treated with 1.81 mL (2.87 mmol) of 20% aqueous titanium (III) chloride in one single portion. The mixture was stirred at rt for 20 min, then made basic with 10% NaOH. The aqueous mixture was extracted with 95:5 CH2Cl2/MeOH. The organic extracts were washed with H2O and saturated NaCl. Evaporation of solvent in vacuo afforded a yellow solid which was filtered through a plug of silica gel, eluting with 90:10 CHCl3/MeOH. The title compound was isolated as a pale yellow solid (0.129 g, 78%): CIMS (NH3, m/z): 359.1 (M++H).

Provenance & Evidence