Thionyl Chloride → HCID 14155692, compound

Participants

Reaction Steps

8.5 ml of thionyl chloride are added dropwise to 1.5 g (4.2×10-3 mol) of α-hydroxy-N,N-dimethyl-6-methyl-2-[4-(methoxymethyl)phenyl]imidazo[1,2-a]pyridine-3-acetamide (IX) dissolved in 85 ml of dry methylene chloride. The mixture is left stirred for 15 h at room temperature and evaporated to dryness, the residue is taken up with pentane, crystallized and dried under vacuum. A white solid is obtained which is dissolved in 120 ml of methylene chloride, 1.9 g (1.2×10-2 mol, 3 eq) of Rongalite are added and the mixture is left stirred for 4 h at room temperature. The mixture is then filtered and the filtrate washed with bicarbonate water and then with water to neutral pH, dried and evaporated. The product is purified by chromatography and crystallized in ether.

Provenance & Evidence