Triethylamine → 2-(4-Chlorobutylthio)pyridine

HRID 2210181Notes

Reaction equation

HRID 2210181 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20]>C(O)C>[Cl:20][CH2:19][CH2:18][CH2:17][CH2:16][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813641-Bromo-4-chlorobutaneHCID 178418616HCID 178418616, compound

Product 1

HCID 190791862-(4-Chlorobutylthio)pyridineYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 25.0 g (225 mmol) of 2-mercaptopyridine and 34.5 ml (247 mmol) of triethylamine in 300 ml of ethanol, 28.5 ml (247 mmol) of 1-bromo-4-chlorobutane was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was dissolved in chloroform. The solution was washed with saturated aqueous sodium bicarbonate and water, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/hexane=1:3) to give 29.73 g of the desired compound (65.5% yield, pale yellow oil).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed with saturated aqueous sodium bicarbonate and water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by column chromatography (eluent: ethyl acetate/hexane=1:3)

Sources & evidence

ORD record
ord-859fe18847ea43cb9d3ec67ea0cc2d32
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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