Carbon Disulfide → 2-[2,5-Dimethyl-2,5-diaza-7,9-dithiabicyclo-(4.3.0)-nonane-8-ylidene]-5-(2-thienyl)-1,3-cyclo hexanedione

HRID 1607059Notes

Reaction equation

HRID 1607059 reaction equation
S(=O)(O)[O-].[Na+].[CH:6]([CH:8]=O)=O.[CH3:10][NH:11][CH2:12][CH2:13][NH:14][CH3:15].S1C=CC(C([O-])=O)S1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH:29]1[CH2:34][C:33](=[O:35])[CH2:32][C:31](=[O:36])[CH2:30]1.[C:37](=[S:39])=[S:38].[OH-].[K+]>O.CN(C)C=O>[CH3:10][N:11]1[CH2:8][CH2:6][N:14]([CH3:15])[CH:13]2[CH:12]1[S:38][C:37](=[C:32]1[C:33](=[O:35])[CH2:34][CH:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)[CH2:30][C:31]1=[O:36])[S:39]2

Participants

9

Reactant 6

HCID 6348Carbon DisulfideHCID 8070N,N'-DimethylethylenediamineHCID 14797Potassium HydroxideHCID 5736855-(2-Thienyl)cyclohexane-1,3-dioneHCID 23706077Sodium;hydrogen sulfite;oxaldehydeHCID 86638310Dithiolate

Product 1

HCID 145168262-[2,5-Dimethyl-2,5-diaza-7,9-dithiabicyclo-(4.3.0)-nonane-8-ylidene]-5-(2-thienyl)-1,3-cyclo hexanedione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2.84 g (0.01 mole) of glyoxal-sodium bisulfite in 20 ml of water was added dropwise at room temperature 1.05 g (0.01 mole) of N,N'-dimethylethylenediamine and the mixture was stirred until it became a homogeneous solution. Then to this solution was added with ice-cooling the dithiolate solution prepared in the manner mentioned below; To a solution of 1.94 g (0.01 mole) of 5-thienyl-1,3-cyclohexanedione and 0.8 g (0.01 mole) of carbon disulfide in 10 ml of dimethylformamide was added with ice-cooling 1.4 g (0.025 mole) of powdered potassium hydroxide, and the mixture was stirred for one hour.

Workup

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

Sources & evidence

ORD record
ord-a644380b59474b3aadcf92f2bd55fb2b
Source dataset
uspto-grants-1989_09
Patent number
US04863925

Reaction notes

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