1,3-Dichloroacetone → Methyl 3-[4-(hydroxymethyl)-1,3-thiazol-2-yl]benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-thiocarbamoyl-benzoic acid methyl ester (7.8 g), 1,3-dichloro-2-propanone (8.4 g) and NaHCO3 (8.4 g) in 1,4-dioxane (180 mL) was heated to 60° C. for 24 h. The reaction mixture was cooled to 20° C. and added to a stirred solution of NaOMe (5.4 g) in MeOH (200 mL). Stirring was continued for 0.5 h. The mixture was poured into ice-cold 2N HCl (200 mL) and the product was extracted with AcOEt. The organic layer was washed with brine, dried and evaporated in vacuum. The residue was crystallized from CH2Cl2/hexane to give 3-(4-hydroxymethyl-thiazol-2-yl)-benzoic acid methyl ester (7.5 g) as light-brown crystals.

Provenance & Evidence