Carbon Disulfide → 2-[1,2,5-Trimethyl-2,5-diaza-7,9-dithiabicyclo(4.3.0)-nonane-8-ylidene]-5,5-dimethyl-1,3-cyclohexanedione

HRID 1607060Notes

Reaction equation

HRID 1607060 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.[CH3:15][C:16]1([CH3:24])[CH2:23][C:21](=[O:22])[CH2:20][C:18](=[O:19])[CH2:17]1.[C:25](=S)=[S:26].[OH-].[K+]>CS(C)=O>[CH3:9][C:10]12[S:26][C:25](=[C:20]3[C:18](=[O:19])[CH2:17][C:16]([CH3:24])([CH3:15])[CH2:23][C:21]3=[O:22])[S:7][CH:11]1[N:5]([CH3:6])[CH2:4][CH2:3][N:2]2[CH3:1]

Participants

7

Reactant 5

HCID 6348Carbon DisulfideHCID 8070N,N'-DimethylethylenediamineHCID 14797Potassium HydroxideHCID 31358DimedoneHCID 86638310Dithiolate

Product 1

HCID 145168272-[1,2,5-Trimethyl-2,5-diaza-7,9-dithiabicyclo(4.3.0)-nonane-8-ylidene]-5,5-dimethyl-1,3-cyclohexanedione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To this solution was added dropwise with ice-cooling 1.94 g (0.022 mole) of N,N'-dimethylethylenediamine and the mixture was stirred for 1 hour. Then to this solution was added with ice-cooling the dithiolate solution prepared in the manner shown below; To a mixture of 2.8 g (0.02 mole) of dimedone and 1.6 g (0.02 mole) of carbon disulfide in 15 ml of dimethylsulfoxide was added 2.7 g (0.044 mole) of powdered potassium hydroxide, and the mixture was stirred for one hour.

Workup

  1. additionTo this solution was added dropwise with ice-
  2. additionThen to this solution was added with ice-
  3. customprepared in the manner
  4. stirringthe mixture was stirred for one hour

Sources & evidence

ORD record
ord-61e1f1bf040442f1a82bf44faca2870c
Source dataset
uspto-grants-1989_09
Patent number
US04863925

Reaction notes

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