Triethylamine → 4-(4-Chlorobutylthio)pyridine

HRID 964162Notes

Reaction equation

HRID 964162 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 4-mercaptopyridine 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-7f05c3424a50446c8f2615d14a3b2f3b
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Reaction notes

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