Triethylamine → 4-(4-Chlorobutylthio)pyridine

HRID 274731Notes

Reaction equation

HRID 274731 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][Cl:13].C(N(CC)CC)C>C(O)C>[Cl:13][CH2:12][CH2:11][CH2:10][CH2:9][S:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813641-Bromo-4-chlorobutaneHCID 178418431pyridine-4-thiol

Product 1

HCID 158169784-(4-Chlorobutylthio)pyridineYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 33.35 g (0.30 mol) of 4mercaptopyridine and 51.44 g (0.30 mol) of 1-bromo-4-chlorobutane in 500 ml of ethanol, 41.9 ml (0.30 mol) of triethylamine was added, and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off and chloroform was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:1) to give 54.27 g of the desired compound (89.7% yield, colorless oil).

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. additionchloroform was added to the residue
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:1)

Sources & evidence

ORD record
ord-a2ab11f6bfd540a7ac19a0758a813ac0
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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