Hydrogen Bromide → HCID 68982787, compound

Participants

Reaction Steps

A solution of 2-(2,6-dichlorobenzyl)-4-(6-methoxy-2-naphthyl)-1,3-thiazole (390 mg, 0.975 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120° C. for 3.5 h and then stood overnight at room temperature. The reaction was concentrated under reduced pressure. The residue was dissolved in 20% methanol-methylene chloride and neutralized with the addition of an excess of 5% NaHCO3. The aqueous layer was separated and extracted three times with 20% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthol (303 mg, 80%) as a brown solid, mp 191-193° C. Elemental Analysis for C20H13Cl2NOS Calc'd: C, 62.19; H, 3.39; N, 3.63. Found: C, 61.31; H, 3.30; N, 3.42.

Provenance & Evidence