Methyl 2,6-dichloroisonicotinate → Methyl 2-chloro-6-(methylthio)isonicotinate

HRID 2233871Notes

Reaction equation

HRID 2233871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Cl)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][S-:14].[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:14][CH3:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 93237Methyl 2,6-dichloroisonicotinateHCID 4378561Sodium methanethiolate

Product 1

HCID 86038391Methyl 2-chloro-6-(methylthio)isonicotinateYield 93.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2,6-dichloroisonicotinate (300 mg, 1.45 mmol) was dissolved in anhydrous DMF. Sodium thiomethoxide (102 mg, 1.45 mmol) was added and the mixture was stirred at room temperature for 4 h. The mixture was diluted with EtOAc and washed with water (×3), brine (×1) and dried over sodium sulfate and concentrated in vacuo to afford title compound (294 mg).

Workup

  1. washwashed with water (×3), brine (×1)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-807917121d6d4000a128ea542c0d8f8e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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