Ethyl Acetate → benzyl 2-cyclohexyl-5,6-dihydro-4H-1,3,4-thiadiazine-5-carboxylate

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Reaction Steps

A solution of 2-bromoprop-2-enoic acid benzyl ester (1.68 g) in dry benzene (10.2 ml) was added to cyclohexane carbothioic acid hydrazide (1.0 g) in dry dimethylformamide (10 ml). The mixture was cooled to 0° and stirred, under an atmosphere of nitrogen, during the gradual addition of 1,5-diazabicyclo[4.3.0]non-5-ene (0.78 g) and then for a further 20 minutes at 0°. Ethyl acetate (100 ml) was added and the mixture was washed with brine and dried over magnesium sulphate The solvent was evaporated under reduced pressure and the resulting oil purified by flash chromatography using 10% ethyl acetate/90% petroleum ether as eluent to yield the sub-title product (1.0 g) as a pink solid.

Provenance & Evidence