Dimethyl acetylenedicarboxylate → Dimethyl 3-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-Xylyl)-4,5-Isothiazoledicarboxylate

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Reaction Steps

A solution of 20.7 g (0.0657 mol) of 5-(α,α,α,α',α',α'-hexafluoro-3,5-xylyl)-1,3,4-oxathiazol-2-one and 18.7 g (0.131 mol) of dimethyl acetylenedicarboxylate in 52 g of o-dichlorobenzene was held at reflux for 10 hours (gas chromatography assay revealed the product had formed in 77% yield) and was concentrated under vacuum to 90° at 0.5 torr. The residue was crystallized from methanol to give 17.9 g of solid, m.p. 71°-74°. The solid was recrystallized to give 14.3 g (53% yield) of white solid, m.p. 73°-75°.

Provenance & Evidence