Acetyl isothiocyanate → N-[5-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-thiazolidin-2-ylidene]-acetamide

Participants

Reaction Steps

An alternative procedure to prepare the titled compound follows. The propargylaniline (Example 22A, 31.08 g, ˜119 mmol) was dissolved into THF (300 mL) and treated with acetylisothiocyanate (11.5 mL, 131 mmol). After being stirred at room temperature briefly, it was heated to approximately 55° C. overnight, and at 60-65° C. for another 6 days. Then the mixture was concentrated and reconcentrated from CH2Cl2/hexanes to give a semi-solid which was mixed into 3:1 Et2O/hexanes and chromatographed on neutral alumina (40% Et2O/hexanes then 40% Et2O/CH2Cl2) to give the titled compound.

Provenance & Evidence