Dimethyl Sulfoxide → Diethyl(1,2,5-trimethyl-2,5-diaza-7,9-dithiabicyclo-[4,3,0]-nonane-8-ylidene)malonate
Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].[S:7]1[CH:11]=[CH:10][CH:9](C([O-])=O)S1.[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[OH-].[K+].[CH3:28][S:29](C)=O>O.C(=S)=S>[CH2:24]([O:23][C:15](=[O:22])[C:16](=[C:28]1[S:29][C:10]2([CH3:9])[CH:11]([N:2]([CH3:1])[CH2:3][CH2:4][N:5]2[CH3:6])[S:7]1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:25]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- additionwas added dropwise at 0° C.
- stirringAfter the reaction mixture was stirred for additional 1 hour
- customThe solid precipitated
- filtrationwas collected by filtration
- customrecrystallized from ethyl acetate-n-hexane
Sources & evidence
- ORD record
- ord-1103fb7d952548deb65996842c80ad08
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04835153
Reaction notes
Loading…