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

Participants

Reaction Conditions

Reaction Steps

Benzothioamide (0.8 g, 5.83 mmol) was dissolved in a mixture EtOH (26.0 ml) and THF (10.4 ml), and the solution was heated to 65° C. 1,3-Dichloropropan-2-one (0.81 g, 6.41 mmol) was added, and the mixture was heated to reflux overnight (UPLC-MS: complete conversion). The solvents were evaporated, and the residue was taken up with EtOAc (100 ml) and washed with an aqueous solution of NaHCO3. The organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude was purified by flash chromatography eluting with petroleum ether/EtOAc=97/3 to obtain 4-chloromethyl-2-phenyl-thiazole (891 mg, 72.9% yield).

Provenance & Evidence