Phosphorus oxychloride → 5-Chloro-3-(2-methylimidazol-1-ylmethyl)-pyridazine

Participants

Reaction Conditions

Reaction Steps

6-(2-Methyl-imidazol-1-ylmethyl)-1H-pyridazin-4-one (3.9 g, 20.5 mmol)) was treated with phosphorus oxychloride (18 ml, 205 mmol) under argon. The mixture was stirred in a 60° C. oilbath for 1.5 hours. The solvent was removed in vacuo and the residue was dissolved in water (100 ml) under icebath cooling. The brown solution was neutralized with solid NaHCO3 and the aqueous layer was extracted with MeCl2 (6×50 ml). The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo to provide 5-chloro-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine (3.1 g, 73%) as a brown solid, MS: m/e=209.3 (M+H+).

Provenance & Evidence