Ethanethiol → Ethyl 4-ethylthio-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

Participants

Reaction Steps

A mixture of 3.0 g (0.009 mol) of product of Example 9, 1.55 g (0.011 mol) of K2CO3 and 3.5 ml (0.047 mol) of ethanethiol in 15 ml of methyl isobutyl ketone was stirred at reflux for 60 hours. The reaction mixture was concentrated. The residue was taken up in ether, washed with 10% NaOH and water, dried (MgSO4) and concentrated in vacuo to 2.98 g of dark oil which was purified by HPLC using 5% ethyl acetate/cyclohexane as eluting solvent affording 2.18 g (69.8%) of product as a tan solid; mp 36°-37.5° C. Anal. Calc'd. for C12H11F6N1O2S1 : C, 41.50; H, 3.19; N, 4.03. Found: C, 41.45; H, 3.22; N, 4.01.

Provenance & Evidence