Saccharin → HCID 555078, compound

HRID 2209443Notes

Reaction equation

HRID 2209443 reaction equation
[Na].[S:2]1(=[O:13])(=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3]1.[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.O>[F:21][C:19]1[C:18]([F:22])=[C:17]([N:3]2[C:4](=[O:11])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:2]2(=[O:12])=[O:13])[C:16]([F:24])=[C:15]([F:14])[N:20]=1

Participants

7

Reactant 4

HCID 5143SaccharinHCID 3633615-Crown-5HCID 69690PentafluoropyridineHCID 5360545Sodium

Product 1

HCID 555078HCID 555078, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of the sodium salt of 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (0.81 g, 3.95 mmol), pentafluoropyridine (0.68 g, 4.0 mmol) and 15-Crown-5 (0.88 g, 4.0 mmol) in acetonitrile (15 ml) was heated to reflux for 6 hours, cooled, and the solvent evaporated in vacuo. The oily residue thus obtained was suspended in water and stirred for 3-4 hours. The solid which percipitated was collected by filtration and dried to afford 1.01 g (77%) of 2-(2,3,5,6-tetrafluoro-4-pyridyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, m.p. 164°-165° C. after recrystallization from carbon tetrachloride.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. temperaturecooled
  4. customthe solvent evaporated in vacuo
  5. customThe oily residue thus obtained
  6. filtrationThe solid which percipitated was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-303c850ea9bb47f7a98731779df3395d
Source dataset
uspto-grants-1995_10
Patent number
US05455255

Reaction notes

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