4-Vinylpyridine → 2-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2-thiazolidine-1,1-dione

HRID 1154325Notes

Reaction equation

HRID 1154325 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[S:9]1(=[O:15])(=[O:14])[CH2:13][CH2:12][CH2:11][NH:10]1>CO>[N:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][N:10]2[CH2:11][CH2:12][CH2:13][S:9]2(=[O:15])=[O:14])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 75024-VinylpyridineHCID 6421571,3-Propanesultam

Product 1

HCID 202664342-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2-thiazolidine-1,1-dioneYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-vinylpyridine (324 g), isothiazolidine-1,1-dioxide (373 g), and "Triton B" solution (129 ml, 40% w/v in methanol) was heated in D.M.F. at 50°-55° for 7 hours. The reaction mixture was then concentrated under vacuum, water (2.52 liters) was added, and the product was extracted into CH2Cl2 (3×1.87 liters). The combined methylene chloride extracts were washed with water and then evaporated to dryness. The residue was dissolved in ethyl acetate (1.3 liters) at 35° and hexane (0.87 liters) was added over 10 minutes. The resulting crystalline product was granulated at -5 to 0° for 4 hours, filtered, washed with hexane (0.37 liters) and dried in vacuum at 25°, to give 2-[2-(4-pyridyl)ethyl]isothiazolidine-1,1-dioxide (518 g).

Workup

  1. temperaturewas heated in D.M.F
  2. concentrationThe reaction mixture was then concentrated under vacuum, water (2.52 liters)
  3. additionwas added
  4. extractionthe product was extracted into CH2Cl2 (3×1.87 liters)
  5. washThe combined methylene chloride extracts were washed with water
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in ethyl acetate (1.3 liters) at 35°
  8. additionhexane (0.87 liters) was added over 10 minutes
  9. waitThe resulting crystalline product was granulated at -5 to 0° for 4 hours
  10. filtrationfiltered
  11. washwashed with hexane (0.37 liters)
  12. customdried in vacuum at 25°

Sources & evidence

ORD record
ord-58215a4347c64f1abf0cc27cfb5107e7
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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