Sodium methanethiolate → 2-Chloro-3-methoxy-5-methylthiomethylpyridine

HRID 1924855Notes

Reaction equation

HRID 1924855 reaction equation
[CH3:1][S-:2].[Na+].[Cl:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13]Cl)=[CH:7][N:6]=1>C(O)C>[Cl:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13][S:2][CH3:1])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 592970732-Chloro-5-(chloromethyl)-3-methoxypyridine

Product 1

HCID 592970842-Chloro-3-methoxy-5-methylthiomethylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of sodium thiomethoxide (0.24 g, 3.5 mmol) in ethanol (10 mL) at 25° C. was added solution of 2-chloro-5-chloromethyl-3-methoxypyridine (0.55 mg, 2.9 mmol) in EtOH (4 mL). The solution was stirred overnight, after which the reaction was concentrated under vacuum. The crude reaction mixture was partitioned between H2O and Et2O and the layers separated. The aqueous phase was further extracted with Et2O (3×) and the combined organic phases dried over MgSO4 and concentrated to furnish 2-chloro-3-methoxy-5-methylthiomethylpyridine as a yellow oil (0.42 g, 71% over two steps). GC-MS: Exact mass calcd for C8H10ClNOS [M]+, 203. Found 203.

Workup

  1. concentrationafter which the reaction was concentrated under vacuum
  2. customThe crude reaction mixture
  3. customwas partitioned between H2O and Et2O
  4. customthe layers separated
  5. extractionThe aqueous phase was further extracted with Et2O (3×)
  6. dry with materialthe combined organic phases dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b24bfacfbd014f6d89a1289f5bd138b3
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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