Nitrogen → 3-Fluoropyridine-2-sulfonamide

HRID 1655067

Reaktionsgleichung

Reaktionsgleichung von HRID 1655067
N[C:2]1[C:3]([S:8]([NH2:11])(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[FH:12].N([O-])=O.[Na+].N#N.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>CS(C)=O>[F:12][C:2]1[C:3]([S:8]([NH2:11])(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 6

HCID 947NitrogenHCID 5234Sodium ChlorideHCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 149437022-Pyridinesulfonamide,3-amino-(9CI)HCID 23668193Sodium Nitrite

Produkt 1

HCID 199579303-Fluoropyridine-2-sulfonamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

5.3 g (0.030 mol) of 3-aminopyridin-2-ylsulfonamide are dissolved in 12 ml of dimethyl sulfoxide, and the solution is added dropwise at 0° C. to 14.3 g (0.72 mol) of hydrogen fluoride (exothermal reaction). 2.4 g (0.035 mol) of sodium nitrite are then added in portions at 0° C. After one hour, the mixture is heated to 70° C. (evolution of N2). After the reaction mixture has cooled, it is added to an ice/water mixture, sodium bicarbonate and sodium chloride are added, and the mixture is then extracted with tetrahydrofuran and ethyl acetate. The combined extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, filtered and evaporated. The residue is stirred in diethyl ether/petroleum ether. Filtration gives 3.7 g of 3-fluoropyridin-2-ylsulfonamide (Compound No. 3.001) of a melting point of +124° to +125° C.

Aufarbeitung

  1. temperatureAfter the reaction mixture has cooled
  2. additionare added
  3. extractionthe mixture is then extracted with tetrahydrofuran and ethyl acetate
  4. washThe combined extracts are washed with a saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-429577d82d2a4a40b7f728b09be5c3bf
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05410063

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