Sodium methanethiolate → HCID 45074565, compound

HRID 884988Notes

Reaction equation

HRID 884988 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 45074565HCID 45074565, compoundYield 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-e181c4e726504c45a1423e4eb93c76cb
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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