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

HRID 1154317Notes

Reaction equation

HRID 1154317 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[NH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.[OH-].[K+].C>ClCCl.C(N(CC)CC)C.C(OCC)(=O)C.C(O)C>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:9]2[CH2:2][CH2:3][CH2:4][S:5]2(=[O:7])=[O:6])=[CH:13][CH:14]=1

Participants

9

Reactant 4

HCID 297MethaneHCID 14797Potassium HydroxideHCID 154103-Chloropropanesulphonyl chlorideHCID 832754-Pyridineethanamine

Product 1

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

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-chloropropanesulphonyl chloride (20.0 g) in dichloromethane (200 cm3) was added dropwise over 1.5 hours to a stirred solution of 4-(2-aminoethyl)pyridine (13.8 g) in dichloromethane (200 cm3) and triethylamine (15 cm3) at 0° C. The ice bath was removed and the mixture was stirred for 16 hours. Saturated aqueous sodium carbonate (100 cm3) was then added and the organic phase was dried (MgSO4) and evaporated in vacuo to yield an oil which was suspended in abs. ethanol (500 cm3) and heated under reflux with potassium hydroxide (6.3 g) for 0.5 hours. The mixture was cooled and filtered and the filtrate was evaporated in vacuo to yield an oil which was taken into warm ethyl acetate (100 cm3), charcoal was added and the mixture was filtered. The filtrate was passed through a "Florisil" column (Trade Mark, Hopkin and Williams) and eluted further with ethyl acetate to obtain a colourless oil. Crystallisation from ethyl acetate gave 2-[2-(4-pyridyl)ethyl]isothiazolidine-1,1-dioxide as colourless needles, m.p. 70° C. (15.0 g).

Workup

  1. customThe ice bath was removed
  2. additionSaturated aqueous sodium carbonate (100 cm3) was then added
  3. dry with materialthe organic phase was dried (MgSO4)
  4. customevaporated in vacuo
  5. customto yield an oil which
  6. temperatureThe mixture was cooled
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo
  9. customto yield an oil which
  10. additionwas added
  11. filtrationthe mixture was filtered
  12. washeluted further with ethyl acetate
  13. customto obtain a colourless oil
  14. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-1f8d39b3458b487b8ee414e907043c0c
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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