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

HRID 2273569Notes

Reaction equation

HRID 2273569 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, concentrated. The residue was purified on silica gel using 5 percent EtOAc in hexane to give 0.57 g of the partially pure 5-[1-(methylthio)ethyl]-2-(trichloromethyl)pyridine (B) in 67 percent 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 percent EtOAc in hexane

Sources & evidence

ORD record
ord-7051a2b4a1ea4ad1ad7798807a962e45
Source dataset
uspto-grants-2015_09
Patent number
US09125412B2

Reaction notes

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