Potassium Hydroxide → Diisopropyl(2,5-diisopropyl-2,5-diaza-7,9-dithiabicyclo-[4,3,0]-nonane-8-ylidene)malonate
Reaction equation
[S:1](=O)(O)[O-].[Na+].[CH:6]([CH:8]=O)=O.[CH:10]([NH:13][CH2:14][CH2:15][NH:16][CH:17]([CH3:19])[CH3:18])([CH3:12])[CH3:11].[S:20]1[CH:24]=CC(C([O-])=O)S1.[C:28]([O:37][CH:38]([CH3:40])[CH3:39])(=[O:36])[CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31].[OH-].[K+]>O.C(=S)=S>[CH:38]([O:37][C:28](=[O:36])[C:29](=[C:24]1[S:20][CH:15]2[CH:14]([N:13]([CH:10]([CH3:12])[CH3:11])[CH2:6][CH2:8][N:16]2[CH:17]([CH3:19])[CH3:18])[S:1]1)[C:30]([O:32][CH:33]([CH3:34])[CH3:35])=[O:31])([CH3:40])[CH3:39]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
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.
Workup
- stirringAfter the mixture was stirred for additional 30 minutes
- filtrationThe solid deposited was collected by filtration
- customrecrystalized from ethyl acetate-n-hexane
Sources & evidence
- ORD record
- ord-502666f2b2fd4074998404aa1ca6c6bb
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04835153
Reaction notes
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