Nitrogen → Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of amino-thioxo-acetic acid ethyl ester (2.03 g. 15.27 mmol) in toluene (16.7 mL) was treated with 1,3-dichloroacetone (2.22 g, 17.50 mmol). The resulting mixture was stirred at reflux for 2 h. EA (20 mL) was added and the org. layer was washed with sat. aq. NaHCO3, brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 hept-EA) gave the title compound as an orange oil. TLC: rf (70:30 hept-EA)=0.40. LC-MS-conditions 02: tR=0.88 min; [M+H]+=206.37.

Provenance & Evidence