Ethyl Acetate → HCID 19843394, compound

Participants

Reaction Steps

Butyl lithium (1.6 M, 7.5 ml) in hexane was added to a solution of the N-propyl thiazole-5-carboxamide (1.7 g, 10 mmol) obtained in A in tetrahydrofuran (80 ml) at -78° C. under an atmosphere of nitrogen. The resultant solution was stirred for 10 minutes and then allowed to warm to room temperature whereupon the 2-(4-chlorophenoxy)-1-(4-chlorophenylsulphonyl)ethane (5.20 g, 15 mmol) obtained in B dissolved in tetrahydrofuran (40 ml) was added. The resultant solution was then refluxed for 5 days. On cooling, the solvent was evaporated and the residue dissolved in 1:4 water: ethyl acetate (500 ml). The organic layer was washed with saturated sodium chloride solution, dried (MgSO4) and the solvent evaporated to leave an oil which, after flash chromatography on silica gel with 1:2 ethylacetate: petroleum ether as the eluant, yielded the desired product (2.42 g). Mass spectroscopy revealed the mass/charge ratio of the parent molecule ion, M+, to be 324 thereby confirming the molecular weight of the product to be 324.

Provenance & Evidence