Sodium methanethiolate → 3-(Methylthio)-2-pyridinecarbonitrile

HRID 1281900Notes

Reaction equation

HRID 1281900 reaction equation
[C:1]([C:3]1[C:8](F)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[CH3:10][S-:11].[Na+]>CN(C=O)C.O>[C:1]([C:3]1[C:8]([S:11][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 70604082-Cyano-3-fluoropyridine

Product 1

HCID 184233573-(Methylthio)-2-pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.00 g (8.19 mmol) of 2-cyano-3-fluoropyridine and 0.631g (9.01 mmol) of sodium thiomethoxide in 8 mL of DMF was stirred at room temperature for 1 h. The reaction mixture was diluted with water (80 mL) and stirred for 5 min. The resulting solid was filtered and dried on a high vacuum line to give 3-1 as an off-white solid: 1H NMR (CDCl3) δ 8.46 (d, 1H, 4.6 Hz), 7.66 (d, 1H, 8.3 Hz), 7.44 (dd, 1H, 4.6, 8.3 Hz), 2.58 (s, 3H).

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried on a high vacuum line

Sources & evidence

ORD record
ord-372e8a832270426eb48c6479de1cfc47
Source dataset
uspto-grants-2002_09
Patent number
US06455532B1

Reaction notes

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