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

HRID 646606Notes

Reaction equation

HRID 646606 reaction equation
Br[CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:13])([F:12])[F: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]([F:13])([F:12])[F:11])=[N:8][CH:9]=1)[CH3:3]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 44227572Pyridine, 5-(1-bromoethyl)-2-(trifluoromethyl)-

Product 1

HCID 248811195-[1-(Methylthio)ethyl]-2-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(1-bromoethyl)-2-trifluoromethylpyridine (1.02 g, 4.0 mmol) in ethanol (30 mL) was cooled to 0° C. under an atmosphere of nitrogen. Sodium methyl mercaptide (364 mg, 5.2 mmol) was added batchwise. Once added, the ice bath was removed and the reaction stirred at room temperature under nitrogen overnight. TLC (9:1, hexane:EtOAc) showed complete reaction. The turbid solution was quenched with water and extracted with ether. The organic layer was then washed with brine and dried (MgSO4). The solvent was removed in vacuo to provide the crude product as a pale yellow liquid, 0.83 g (93%); 1H NMR (CDCl3) δ 8.65 (s, 1H), 7.89 (d, 1H), 7.67 (d, 1H), 3.93 (q, 1H), 1.94 (s, 3H), 1.62 (d, 3H).

Workup

  1. additionOnce added
  2. customthe ice bath was removed
  3. customreaction
  4. customThe turbid solution was quenched with water
  5. extractionextracted with ether
  6. washThe organic layer was then washed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8233f7d63c1743058394966fa4f02622
Source dataset
uspto-grants-2010_04
Patent number
US07705154B2

Reaction notes

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