HCID 13712049, compound → HCID 21291364, compound

HRID 622627Notes

Reaction equation

HRID 622627 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[NH:6]1[CH2:10][CH2:9][CH:8](OS(C2C=CC(C)=CC=2)(=O)=O)[C:7]1=[O:22]>CC(C)=O>[C:1]([O:4][CH:8]1[CH2:9][CH2:10][NH:6][C:7]1=[O:22])(=[S:3])[CH3:2]

Participants

4

Reactant 2

HCID 13712049HCID 13712049, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 21291364HCID 21291364, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 855 mg. (7.5 mmoles) potassium thioacetate and 1.27 g (5 mmoles) crude 2-pyrrolidon-3-yl-p-toluenesulfonate in 40 ml. acetone was refluxed under nitrogen for ca. 20 hr. The mixture was then filtered and the filtrate was concentrated in vacuo. The residue was partitioned between 50 ml. ethyl acetate and 50 ml. water and the ethyl acetate layer was washed with 40 ml. water and 40 ml. saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was chromatographed on silica gel, eluting with ethyl acetate, to yield 180 mg. (23% yield) of the title compound.

Workup

  1. additionA mixture of 855 mg
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between 50 ml
  5. washwater and the ethyl acetate layer was washed with 40 ml
  6. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed on silica gel
  9. washeluting with ethyl acetate
  10. customto yield 180 mg

Sources & evidence

ORD record
ord-3d42457397774f9ba4b38505a4a8684c
Source dataset
uspto-grants-1988_09
Patent number
US04772597

Reaction notes

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