1-Bromo-3-chloropropane → 4-[(3-Chloropropyl)sulfanyl]pyridine

HRID 1614545Notes

Reaction equation

HRID 1614545 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][Cl:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl: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 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178418431pyridine-4-thiol

Product 1

HCID 158169844-[(3-Chloropropyl)sulfanyl]pyridineYield 86.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-mercaptopyridine (5.0 g), 1-bromo-3-chloropropane (14.2 g), and anhydrous potassium carbonate in 250 mL acetone is refluxed under nitrogen for 1 hour. The mixture is cooled, filtered and concentrated. The residue is taken up into diethyl ether and washed with brine, dried over magnesium sulfate and evaporated in vacuo. The crude product is purified by column chromatography (silica; hexane: ethyl acetate, 50:50) to give the title compound (7.34 g) as a colorless oil which is used directly in further transformations.

Workup

  1. temperatureis refluxed under nitrogen for 1 hour
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe crude product is purified by column chromatography (silica; hexane: ethyl acetate, 50:50)

Sources & evidence

ORD record
ord-29a928164b1042c4aa7ac1d4bbe200b5
Source dataset
uspto-grants-1993_03
Patent number
US05198443

Reaction notes

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