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

HRID 1450462Notes

Reaction equation

HRID 1450462 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][CH:13]([CH3:15])[CH3:14].[F:16][C:17]1[N:22]=[C:21]([F:23])[C:20]([F:24])=[C:19](F)[C:18]=1[F:26].C1OCCOCCOCCOCCOC1>C(#N)C>[F:23][C:21]1[C:20]([F:24])=[C:19]([N:6]2[C:5](=[O:10])[CH:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[N:3]([CH3:2])[S:7]2(=[O:9])=[O:8])[C:18]([F:26])=[C:17]([F:16])[N:22]=1

Participants

6

Reactant 4

HCID 3633615-Crown-5HCID 69690PentafluoropyridineHCID 5360545SodiumHCID 189222624-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 189222552-(2,3,5,6-Tetrafluoro-4-pyridyl)-5-methyl-4-(3-methylbutyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of the sodium salt of 5-methyl-4-(3-methylbutyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 4.13 mmol, prepared by treatment with sodium methoxide), pentafluoropyridine (0.54 ml, 4.97 mmol), and 0.91 g (4.13 mmol) of 15-Crown-5 suspended in 30 ml of acetonitrile was refluxed for 17 hours. The mixture was cooled, concentrated in vacuo, and the residue extracted with methylene chloride, and the organic layer was washed with water (3x) and brine. After drying over sodium sulfate, the organic layer was concentrated in vacuo and a crude product was purified by flash chromatography (10% ethyl acetate in hexane) to afford 0.62 g (41%) of 2-(2,3,5,6-tetrafluoro-4-pyridyl)-5-methyl-4-(3-methylbutyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =(CH2)2CH(CH3)2 ; R2 =H; R3 =CH3), as a solid, m.p. 80.5°-81.5° C.

Workup

  1. temperaturewas refluxed for 17 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. extractionthe residue extracted with methylene chloride
  5. washthe organic layer was washed with water (3x) and brine
  6. dry with materialAfter drying over sodium sulfate
  7. concentrationthe organic layer was concentrated in vacuo
  8. customa crude product was purified by flash chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ec824216e14d4c6c8eaaf1cdcd31a682
Source dataset
uspto-grants-1997_02
Patent number
US05602154

Reaction notes

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