Carbon Disulfide → 2-[2-Methyl-2,5-diaza-7,9-dithiabicyclo-(4,3, 0)-nonane-8-ylidene]-5,5-dimethyl-1,3-cyclohexanedione

HRID 1607058Notes

Reaction equation

HRID 1607058 reaction equation
S(=O)(O)[O-].[Na+].[CH:6]([CH:8]=O)=O.[CH3:10][NH:11][CH2:12][CH2:13][NH2:14].S1C=CC(C([O-])=O)S1.[CH3:23][C:24]1([CH3:32])[CH2:31][C:29](=[O:30])[CH2:28][C:26](=[O:27])[CH2:25]1.[C:33](=[S:35])=[S:34].[OH-].[K+]>O.CS(C)=O>[CH3:10][N:11]1[CH2:8][CH2:6][NH:14][CH:13]2[CH:12]1[S:34][C:33](=[C:28]1[C:26](=[O:27])[CH2:25][C:24]([CH3:32])([CH3:23])[CH2:31][C:29]1=[O:30])[S:35]2

Participants

9

Reactant 6

HCID 6348Carbon DisulfideHCID 8014N-MethylethylenediamineHCID 14797Potassium HydroxideHCID 31358DimedoneHCID 23706077Sodium;hydrogen sulfite;oxaldehydeHCID 86638310Dithiolate

Product 1

HCID 145168202-[2-Methyl-2,5-diaza-7,9-dithiabicyclo-(4,3, 0)-nonane-8-ylidene]-5,5-dimethyl-1,3-cyclohexanedione

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 5.68 g (0.02 mole) of glyoxal-sodium bisulfite in 30 ml of water was added dropwise with ice-cooling 1.5 g (0.02 mole) of N-methyl-ethylenediamine. Then to this solution was added dropwise with ice-cooling the dithiolate solution prepared in the manner shown below; To mixture of 2.8 g (0.02 mole) of dimedone and 1.6 g (0.021 mole) of carbon disulfide in 20 ml of dimethylsulfoxide was added at room temperature 2.7 g (0.044 mole) of powdered potassium hydroxide and the mixture was stirred for 1 hour.

Workup

  1. additionwas added dropwise with ice-
  2. additionThen to this solution was added dropwise with ice-
  3. customprepared in the manner

Sources & evidence

ORD record
ord-8cc7f082d6cc4a329f2bde042e2d4d0f
Source dataset
uspto-grants-1989_09
Patent number
US04863925

Reaction notes

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