15-Crown-5 → 2-(2,3,5,6-Tetrafluoro-4-pyridyl)-5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1289627Notes

Reaction equation

HRID 1289627 reaction equation
[Na].[CH3:2][N:3]1[S:7](=[O:9])(=[O:8])[NH:6][C:5](=[O:10])[CH:4]1[CH2:11][CH2:12][CH3:13].[F:14][C:15]1[N:20]=[C:19]([F:21])[C:18]([F:22])=[C:17](F)[C:16]=1[F:24].C1OCCOCCOCCOCCOC1>C(#N)C.CN(C=O)C>[F:21][C:19]1[C:18]([F:22])=[C:17]([N:6]2[C:5](=[O:10])[CH:4]([CH2:11][CH2:12][CH3:13])[N:3]([CH3:2])[S:7]2(=[O:9])=[O:8])[C:16]([F:24])=[C:15]([F:14])[N:20]=1

Participants

7

Reactant 4

HCID 3633615-Crown-5HCID 69690PentafluoropyridineHCID 5360545SodiumHCID 189222534-Propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 98409172-(2,3,5,6-Tetrafluoro-4-pyridyl)-5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of the sodium salt of 5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.2 mmol, prepared by treatment with sodium methoxide) suspended in 30 ml of acetonitrile was added pentafluoropyridine (0.57 ml, 5.2 mmol) and 1.14 g (5.17 mmol) of 15-Crown-5 and DMF (25 ml), and the resulting mixture was refluxed for 20 hours. The mixture was cooled, concentrated in vacuo, and the residue diluted with water, extracted with methylene chloride, and the organic layer was washed with water and brine. The organic layer was concentrated in vacuo and a crude product was purified by flash chromatography to afford 0.39 g (22%) of 2-(2,3,5,6-tetrafluoro-4-pyridyl)-5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =propyl; R2 =H; R3 =CH3).

Workup

  1. temperaturethe resulting mixture was refluxed for 20 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. additionthe residue diluted with water
  5. extractionextracted with methylene chloride
  6. washthe organic layer was washed with water and brine
  7. concentrationThe organic layer was concentrated in vacuo
  8. customa crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-90043742b52e4bb5be512aed19671bf8
Source dataset
uspto-grants-1998_05
Patent number
US05750546

Reaction notes

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