Hydrochloric Acid → HCID 14500722, compound

Participants

Reaction Steps

A stirred slurry of 18.7 g (0.093 mole) of 4-cyclooctyl-3-thiosemicarbazide in 150 mL of absolute ethanol under nitrogen atmosphere was treated with 16.5 g (0.1 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 1.5 hr, treated with 50 mL of 2N ethanolic hydrogen chloride and heated at reflux for ~16 hr. The yellow-brown reaction mixture was filtered and concentrated in vacuo to a dark oil which solidified. Trituration of the crude product with warm acetone removed most of the color to give 17.9 g of product. Recrystallization from methyl ethyl ketone/isopropyl ether followed by recrystallization from methyl ethyl ketone gave 7.1 g of crystalline product, mp 161°-166° C. which was dried at 82° C. under reduced pressure for 3 hr (mp, 168°-171° C.).

Provenance & Evidence