Glyoxal → Diisopropyl(2,5-dimethyl-2,5-diaza-7,9-dithiabicyclo-[4,3,0]-nonane-8-ylidene)malonate

Participants

Reaction Steps

In 10 ml of water was dissolved 3.2 g of 40% aqueous glyoxal and 1.9 g of N,N'-dimethylethylenediamine at 0° C. To this solution was added 4.4 g of sodium bisulfite dissolved in 20 ml of water and the mixture was stirred for 30 minutes. To this was added dropwise at 0° C. the dithiolate solution which had been prepared previously by the reaction of 3.7 g of diisopropyl malonate with 1.8 g of carbon disulfide in the presence of 8 g of 30% aqueous potassium hydroxide. After the reaction mixture was stirred for additional 3 hours, 50 ml of water was added to the reaction solution. The solid deposited was collected by filtration and recrystalized from ethyl acetate-n-hexane to give 5.5 g of the desired product.

Provenance & Evidence