Sodium methanethiolate → 2,5-Dichloro-4-methyl-6-(methylthio)nicotinonitrile

HRID 656638Notes

Reaction equation

HRID 656638 reaction equation
[Cl:1][C:2]1[N:9]=[C:8](Cl)[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1[C:4]#[N:5].[CH3:13][S-:14].[Na+]>CO>[Cl:1][C:2]1[N:9]=[C:8]([S:14][CH3:13])[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 336978792,5,6-Trichloro-4-methylnicotinonitrile

Product 1

HCID 576643972,5-Dichloro-4-methyl-6-(methylthio)nicotinonitrileYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a slurry of 2,5,6-trichloro-4-methyl-nicotinonitrile (10.0 g, 45.2 mmol, Tetrahedron, 1977, 33, 113-117) in MeOH (150 ml) at 0° C. is added solid sodium thiomethoxide (3.33 g, 45.2 mmol). The mixture is stirred at 0° C. for 1 hour, then room temperature for 1 hour. The reaction is quenched by the addition of water (250 ml). The mixture is partitioned between water and EtOAc (500 ml each), and the layers are shaken and separated. The organic layer is dried (anhydrous magnesium sulfate), filtered, and concentrated to give the title compound as a yellow solid (10.5 g, 99%). Mass (m/z): 233.0 (M++1).

Workup

  1. waitroom temperature for 1 hour
  2. customThe reaction is quenched by the addition of water (250 ml)
  3. customThe mixture is partitioned between water and EtOAc (500 ml each)
  4. stirringthe layers are shaken
  5. customseparated
  6. dry with materialThe organic layer is dried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c2a67393a61470aa2d8ebd88a9c027d
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

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