Sodium methanethiolate → 3-(Methylsulfanyl)pyridine-4-carbonitrile

HRID 2190866Notes

Reaction equation

HRID 2190866 reaction equation
Cl[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][S-:11].[Na+]>CN(C=O)C>[CH3:10][S:11][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 106783063-Chloropyridine-4-carbonitrile

Product 1

HCID 450745653-(Methylsulfanyl)pyridine-4-carbonitrileYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2.0 g of 3-chloroisonicotinonitrile and 8 ml of DMF, 1.02 g of sodium thiomethoxide was added while ice-cooling. The reaction mixture was stirred at 0° C. for one hour. The reaction mixture was concentrated under reduced pressure, to which ethyl acetate was added for filtering out insoluble matters. Filtrates were concentrated under reduced pressure, and the resultant residue was subjected to silica gel column chromatography to give 2.11 g of 3-methylthioisonicotinonitrile.

Workup

  1. additionwas added while ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure, to which ethyl acetate
  4. additionwas added
  5. filtrationfor filtering out insoluble matters
  6. concentrationFiltrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-091e6ac13df044a3ac321e2fbe9810a2
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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