Dimethyl Sulfoxide → Diethyl(1,2,5-trimethyl-2,5-diaza-7,9-dithiabicyclo-[4,3,0]-nonane-8-ylidene)malonate

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Reaction Steps

In 40 ml of water was suspended 11.2 g of pyruvic aldehyde sodium bisulfite addition compound, and 2.3 g of N,N'-dimethylethylenediamine was added dropwise at 0° C. and the mixture was stirred for additional 1 hour. To this solution was added dropwise at 0° C. the dithiolate solution, which had been prepared previously by the reaction of 3.2 g of diethyl malonate with 1.8 g of carbon disulfide in 20 ml of dimethylsulfoxide in the presence of 9.7 g of 30% aqueous potassium hydroxide. After the reaction mixture was stirred for additional 1 hour, 50 ml of water was added to the solution. The solid precipitated was collected by filtration and recrystallized from ethyl acetate-n-hexane to give 1.7 g of the desired product.

Provenance & Evidence