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

HRID 1762814Notes

Reaction equation

HRID 1762814 reaction equation
[S:1](=O)(O)[O-].[Na+].[CH:6]([CH:8]=O)=O.[CH2:10]([NH2:14])[CH:11]([NH2:13])[CH3:12].[S:15]1[CH:19]=CC(C([O-])=O)S1.[C:23]([O:32][CH:33]([CH3:35])[CH3:34])(=[O:31])[CH2:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26].[OH-].[K+]>O.C(=S)=S>[CH:33]([O:32][C:23](=[O:31])[C:24](=[C:19]1[S:15][CH:6]2[CH:8]([NH:14][CH2:10][CH:11]([CH3:12])[NH:13]2)[S:1]1)[C:25]([O:27][CH:28]([CH3:29])[CH3:30])=[O:26])([CH3:35])[CH3:34]

Participants

8

Reactant 5

HCID 6567PropylenediamineHCID 14797Potassium HydroxideHCID 83223Diisopropyl malonateHCID 23706077Sodium;hydrogen sulfite;oxaldehydeHCID 86638310Dithiolate

Product 1

HCID 15623895Diisopropyl(3-methyl-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 17.4 g of glyoxal sodium bisulfite in 120 ml of water was added dropwise 7.1 g of propylenediamine at 0° C. and the mixture was stirred for 1 hour. Then to this solution was added dropwise at 0° C. the dithiolate solution, which had been prepared previously as follow; To a mixture of 15.04 g of diisopropyl malonate and 6.4 g of carbon disulfide was added dropwise with ice-cooling 23.8 g of 45% aqueous potassium hydroxide solution and was stirred at the same temperature for 1 hour.

Workup

  1. customhad been prepared previously
  2. additionwas added dropwise with ice-
  3. stirringwas stirred at the same temperature for 1 hour

Sources & evidence

ORD record
ord-4c76e46961474d59b4587e95eecabe51
Source dataset
uspto-grants-1989_05
Patent number
US04835153

Reaction notes

Loading…