Glyoxal → Diisopropyl(2,5-dimethyl-2,5-diaza-7,9-dithiabicyclo-[4,3,0]-nonane-8-ylidene)malonate
Reaction equation
[CH:1]([CH:3]=O)=O.[CH3:5][NH:6][CH2:7][CH2:8][NH:9][CH3:10].[S:11](=O)(O)[O-].[Na+].[S:16]1[CH:20]=CC(C([O-])=O)S1.[C:24]([O:33][CH:34]([CH3:36])[CH3:35])(=[O:32])[CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].[OH-].[K+]>O.C(=S)=S>[CH:34]([O:33][C:24](=[O:32])[C:25](=[C:20]1[S:16][CH:1]2[CH:3]([N:6]([CH3:5])[CH2:7][CH2:8][N:9]2[CH3:10])[S:11]1)[C:26]([O:28][CH:29]([CH3:30])[CH3:31])=[O:27])([CH3:36])[CH3:35]Participants
9
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- stirringAfter the reaction mixture was stirred for additional 3 hours
- filtrationThe solid deposited was collected by filtration
- customrecrystalized from ethyl acetate-n-hexane
Sources & evidence
- ORD record
- ord-4d8c9a12c6e74000921e9186c0a1569e
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04835153
Reaction notes
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