Sodium methanethiolate → 2-Methoxy-6-methylsulfanyl-isonicotinic acid methyl ester

HRID 559675Notes

Reaction equation

HRID 559675 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6](Cl)[CH:5]=1.[CH3:14][S-:15].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([S:15][CH3:14])[N:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

Product 1

HCID 592784982-Methoxy-6-methylsulfanyl-isonicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-chloro-6-methoxy-isonicotinic acid methyl ester (8.5 g, 42 mmol) in DMF (100 mL) was added sodium thiomethoxide (3.22 g, 41.6 mmol), resulting in a yellow colored solution. After 18 hours, the mixture was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuo to afford 2-methoxy-6-methylsulfanyl-isonicotinic acid methyl ester.

Workup

  1. customresulting in a yellow colored solution
  2. customthe mixture was quenched with saturated aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (4×50 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc1c5e5ca14d4c5089cbe6661102f1da
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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