Hydrochloric Acid → HCID 20566530, compound

Participants

Reaction Steps

A solution of ethyl N-amino-N-(3'-hydroxy-3-methylnonyl)carbamate (1.812 g; 6.97 mmole), and methyl isothiocyanate (764 mg; 10.5 mmole) in dry toluene (25 ml) was heated under refulx for 2 hrs and then allowed to cool to room temperature. Potassium t-butoxide (1,56 g; 13.96 mmole) was added and the mixture stirred at 25° for 16 hr. The mixture was portitioned between water (100 ml) and ethyl acetate (100 ml) and acidified with 5 M HCl. The aqueous layer was extracted with ethyl acetate (50 ml) and the combined organic layers washed with water (2×100 ml) and brine (100 ml), dried (Na2SO4), and evaporated to dryness and chromatography of the residue on Kieselgel 60 (10 g) in chloroform gave 2-(3'-hydroxy-3'-methylnonyl)-4-methyl-1,2,4-triazolidine-3-one-5-thione as a gum (1.83 g; 91%).

Provenance & Evidence