Reaction #1849994

Reaction equation

diisopropyl malonate

potassium hydroxide

glyoxal sodium bisulfite

N,N'-diisopropylethylenediamine

dithiolate

→

desired product

Yield 45.0%

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

Yield 45.0%

Solvents

water

carbon disulfide

water

Conditions

Workup

1. 1
   workup.STIRRINGAfter the mixture was stirred for additional 30 minutes
2. 2
   FiltrationThe solid deposited was collected by filtration
3. 3
   Otherrecrystalized from ethyl acetate-n-hexane

Procedure

To a suspension of 1.7 g of glyoxal sodium bisulfite in 12 ml of water was added N,N'-diisopropylethylenediamine dropwise at room temperature and the mixture was stirred until it became a homogeneous solution. To this solution was added dropwise at 0° C. the dithiolate solution which had been prepared previously by the reaction of 1.13 g of diisopropyl malonate with 0.55 g of carbon disulfide in the presence of 2.9 g of 30% aqueous potassium hydroxide. After the mixture was stirred for additional 30 minutes, 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 1.16 g of the desired product.

Source