3-Aminopyridine → HCID 178503894, compound

HRID 479504Notes

Reaction equation

HRID 479504 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][S:9][C:10](SC)=[N:11][C:12]#[N:13]>C(#N)C>[C:12]([N:11]=[C:10]([S:9][CH3:8])[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)#[N:13]

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 66289Dimethyl N-cyanodithioiminocarbonate

Product 1

HCID 178503894HCID 178503894, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-aminopyridine (5.16 g, 54.8 mmol) and dimethyl N-cyanodithioiminocarbonate (8.02 g, 54.8 mmol) in acetonitrile (200 mL) was heated at reflux for 6 days. The solution was cooled and concentrated to a volume of 75 mL where upon a white solid precipitated from solution. The solid was collected by filtration and washed with 50% ether/hexanes (500 mL) to provide 7.79 g of the desired product as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 days
  3. temperatureThe solution was cooled
  4. concentrationconcentrated to a volume of 75 mL where upon a white solid
  5. customprecipitated from solution
  6. filtrationThe solid was collected by filtration
  7. washwashed with 50% ether/hexanes (500 mL)

Sources & evidence

ORD record
ord-15c762d63d504a0dad940df24eb4d0e1
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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