Carbon Disulfide → triethylammonium N-(2-pyrazinyl)-dithiocarbamate

HRID 51982Notes

Reaction equation

HRID 51982 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:7]=1.[C:8](=[S:10])=[S:9].C(OCC)(=O)C.[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18]>CCCCCC>[N:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:8](=[S:9])[S-:10].[CH2:17]([NH+:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 78747Aminopyrazine

Product 1

HCID 19962701triethylammonium N-(2-pyrazinyl)-dithiocarbamateYield 31.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a 100-ml flask, 4.9 g (50 mmol) of 3-aminopyrazine, 4.5 g (59 mmol) of carbon disulfide and 50 ml of ethyl acetate were placed, and 6.5 g (64 mmol) of triethylamine was added dropwise with stirring over a 5-min period on a water bath. After the mixture was stirred at 60° C. for 5 hr. 10 ml of hexane was added to the mixture, which was allowed to stand overnight at room temperature to precipitate yellow crystals. The crystals were separated from the solution by filtration, and washed with 5 ml of ethyl acetate to obtain 4.3 g of triethylammonium N-(2-pyrazinyl)-dithiocarbamate (Intermediate II-1). Yield 31%. Mp 113°-116° C. (dec).

Workup

  1. stirringAfter the mixture was stirred at 60° C. for 5 hr
  2. customto precipitate yellow crystals
  3. customThe crystals were separated from the solution by filtration
  4. washwashed with 5 ml of ethyl acetate

Sources & evidence

ORD record
ord-44ea6459c73449988937bfaeef87df1a
Source dataset
uspto-grants-1997_04
Patent number
US05616456

Reaction notes

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