Water → 2-(Chloromethyl)-4-phenyl-1,3-thiazole

Participants

Reaction Steps

Thionyl chloride (6.25 g, 0.052 mole) was added dropwise to a stirred solution of 2-hydroxymethyl-4-phenylthiazole (9.55 g; 0.05 mole) and dry pyridine (4.0 g; 0.051 mole) in dry benzene (60 ml) held at room temperature. The mixture was stirred and heated to boiling for 1 hour. The cooled reaction mixture was then shaken with 2 × 70 ml H2O and dried over anhydrous MgSO4. The solvent was removed under vacuum and the remaining red oil extracted with 40°-60° C. petroleum ether (100 ml), discarding a small tarry residue. The extract was treated with decolourising charcoal, filtered and evaporated, leaving a yellow-red oil that crystallised on refrigeration.

Provenance & Evidence