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

HRID 1762810Notes

Reaction equation

HRID 1762810 reaction equation
[S:1](=O)(O)[O-].[Na+].[CH:6]([CH:8]=O)=O.[CH2:10]([NH2:13])[CH2:11][NH2:12].[S:14]1[CH:18]=CC(C([O-])=O)S1.[C:22]([O:31][CH:32]([CH3:34])[CH3:33])(=[O:30])[CH2:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25].[OH-].[K+]>O.C(=S)=S>[CH:32]([O:31][C:22](=[O:30])[C:23](=[C:18]1[S:14][CH:10]2[CH:11]([NH:12][CH2:6][CH2:8][NH:13]2)[S:1]1)[C:24]([O:26][CH:27]([CH3:28])[CH3:29])=[O:25])([CH3:34])[CH3:33]

Participants

8

Reactant 5

HCID 3301EthylenediamineHCID 14797Potassium HydroxideHCID 83223Diisopropyl malonateHCID 23706077Sodium;hydrogen sulfite;oxaldehydeHCID 86638310Dithiolate

Product 1

HCID 15623881Diisopropyl(2,5-diaza-7,9-dithiabicyclo-[4,3,0]-nonane-8-ylidene)malonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

To a suspension of 2.5 g of glyoxal-sodium bisulfite in 10 ml of water was added dropwise 0.5 g of ethylenediamine with ice-cooling and the mixture was stired for additional 1 hour. To this solution was added dropwise with ice-cooling the dithiolate aqueous solution which had been prepared previously by the reaction of 1.5 g of diisopropyl malonate with 0.8 g of carbon disulfide in the presence of 3.3 g of 30% aqueous potassium hydroxide.

Workup

  1. temperaturecooling
  2. additionTo this solution was added dropwise with ice-

Sources & evidence

ORD record
ord-7c06ca2c358b4497b3c15f7713df0052
Source dataset
uspto-grants-1989_05
Patent number
US04835153

Reaction notes

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