Potassium Carbonate → 4-(2-Propynylthio)pyridine

HRID 27042

Reaction equation

HRID 27042 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](Cl)[C:15]#[CH:16]>CS(C)=O>[CH2:16]([S:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[C:15]#[CH:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 178418431pyridine-4-thiol

Product 1

HCID 233434934-(2-Propynylthio)pyridineYield 40.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

In 200 ml dimethyl sulfoxide (DMSO) was dissolved 25.0 g (0.225 mole) 4-mercaptopyridine. To this solution were added 15.5 g (0.112 mole) anhydrous potassium carbonate and 16.5 g (0.25 mole) propargyl chloride. This mixture was heated at 60° C. for 3 hours. The reaction mixture was then cooled to room temperature and filtered. The filtrate was added to an equal volume of water. This mixture was extracted with ether. After removal of the ether under reduced pressure, there remained 20.0 g crude product. Distillation gave 13.5 g 4-(2-propynylthio)pyridine. Yield 39% theory; b.p. 79°-81° C. (1.0 mm); mp 55°-56° C.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate was added to an equal volume of water
  4. extractionThis mixture was extracted with ether
  5. customAfter removal of the ether under reduced pressure, there
  6. distillationDistillation

Sources & evidence

ORD record
ord-75984f85d1ae4df1a43913435b44f7c4
Source dataset
uspto-grants-1980_09
Patent number
US04220577

Linked notes

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