Carbon Disulfide → HCID 86743144, compound

HRID 1904690Notes

Reaction equation

HRID 1904690 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8](=[S:10])=[S:9].[CH2:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12]>C1C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:8](=[S:9])[S-:10])[CH:3]=1.[CH2:11]([NH+:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 100093-Aminopyridine

Product 1

HCID 86743144HCID 86743144, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 9.4 g 3-aminopyridine and 7.6 g carbon disulfide in 100 ml benzene, was added dropwise 14 ml triethylamine, the mixture was stirred at room temperature for three hours, and the two separate layers thus formed were allowed to stand overnight. The benzene layer was removed by decantation, the oily product was washed four times with 30 ml ether, and the solvent was distilled off under reduced pressure, affording triethylammonium (3-pyridyl)dithiocarbamate. This crude salt was dissolved in 75 ml chloroform, 14 ml triethylamine was added, and the resulting solution was cooled in ice. Ethyl chloroformate (10.2 ml) was then added dropwise, the reaction was allowed to proceed at room temperature for one hour, and the reaction mixture was washed with 50 ml water, dried over anhydrous sodium sulfate and concentrated under reduced pressure, giving 13.2 g of crude 3-pyridyl isothiocyanate as oil.

Workup

  1. customthe two separate layers
  2. customthus formed
  3. waitto stand overnight
  4. customThe benzene layer was removed by decantation
  5. washthe oily product was washed four times with 30 ml ether
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4b8e53b4a5cd42d886c12773f24fc65d
Source dataset
uspto-grants-1989_06
Patent number
US04839376

Reaction notes

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