Potassium Fluoride → HCID 69444790, compound

HRID 446171Notes

Reaction equation

HRID 446171 reaction equation
[F-].[K+].[O:3]=[S:4]1(=[O:38])[N:8](S(C2C=CC(C)=CC=2)(=O)=O)[C:7]2[CH:19]=[C:20]([CH2:23][N:24]([C:30]3[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=3)[N:25]3[CH:29]=[CH:28][N:27]=[CH:26]3)[CH:21]=[CH:22][C:6]=2[O:5]1>O.C(#N)C>[O:38]=[S:4]1(=[O:3])[NH:8][C:7]2[CH:19]=[C:20]([CH2:23][N:24]([C:30]3[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=3)[N:25]3[CH:29]=[CH:28][N:27]=[CH:26]3)[CH:21]=[CH:22][C:6]=2[O:5]1

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 69440334HCID 69440334, compound

Product 1

HCID 69444790HCID 69444790, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Potassium fluoride (0.36 g, 6.14 mmol) in water (5 ml) was added to 4[N-[(2,2-dioxido-3-tosyl-3H-1,2,3-benzoxathiazol-5-yl)methyl]-N-(1H-imidazol-1-yl)amino]benzonitrile (1.60 g, 3.07 mmol) in acetonitrile (15 ml) at room temperature. The solution was stirred overnight, concentrated, extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under vacuum. Flash chromatography on silica gel (toluene/dioxane: 5/5) yielded an oil and crystallization from ethanol yielded the expected product (0.17 g, 15%, mp: 230° C.).

Workup

  1. concentrationconcentrated
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customFlash chromatography on silica gel (toluene/dioxane: 5/5) yielded
  6. customan oil and crystallization from ethanol

Sources & evidence

ORD record
ord-db92d2e3f3ab4e2c812df147f749f930
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

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