Sodium methanethiolate → 5-[1-(Methylthio)ethyl]-2-(trichloromethyl)pyridine

HRID 2355767Notes

Reaction equation

HRID 2355767 reaction equation
Br[CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([Cl:13])([Cl:12])[Cl:11])=[N:8][CH:9]=1)[CH3:3].[CH3:14][S-:15].[Na+]>C(O)C>[CH3:14][S:15][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([Cl:13])([Cl:12])[Cl:11])=[N:8][CH:9]=1)[CH3:3]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 592186385-(1-Bromoethyl)-2-(trichloromethyl)pyridine

Product 1

HCID 592186205-[1-(Methylthio)ethyl]-2-(trichloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(1-bromoethyl)-2-(trichloromethyl)pyridine (A) (0.95 g, 3.14 mmol) in ethanol (15 mL) was treated with sodium thiomethoxide (0.44 g, 6.29 mmol) portionwise at 0° C. The mixture was stirred at room temperature overnight. The solvent ethanol was then removed under a reduced pressure and the residue was re-taken into CH2Cl2 and brine. The two phases were separated and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified on silica gel using 5% EtOAc in hexane v/v to give 0.57 g of the partially pure 5-[1-(methylthio)ethyl]-2-(trichloromethyl)pyridine (B) in 67% crude yield. GC-MS: mass calcd for C9H10Cl3NS [M]+ 269. Found 269.

Workup

  1. customThe solvent ethanol was then removed under a reduced pressure
  2. customThe two phases were separated
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using 5% EtOAc in hexane v/v

Sources & evidence

ORD record
ord-a2352c99fa3a42909ad7b81014d4eb28
Source dataset
uspto-grants-2010_07
Patent number
US07754888B2

Reaction notes

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