Acetonitrile → 5-chloro-2,4-difluoro-N-pyridazin-3-ylbenzenesulfonamide

HRID 46392

Reaktionsgleichung

Reaktionsgleichung von HRID 46392
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[N:2]=1.C1N2CCN(CC2)C1.[Cl:16][C:17]1[C:18]([F:28])=[CH:19][C:20]([F:27])=[C:21]([S:23](Cl)(=[O:25])=[O:24])[CH:22]=1.C(#N)C>>[Cl:16][C:17]1[C:18]([F:28])=[CH:19][C:20]([F:27])=[C:21]([S:23]([NH:7][C:3]2[N:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:25])=[O:24])[CH:22]=1

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 9237DabcoHCID 230373AminopyridazineHCID 27735275-Chloro-2,4-difluorobenzenesulphonyl chloride

Produkt 1

HCID 594365565-chloro-2,4-difluoro-N-pyridazin-3-ylbenzenesulfonamideAusbeute 24,9 %

Versuchsvorschrift

Pyridazin-3-amine (1.00 g, 10.5 mmol) and triethylenediamine (1.18 g, 10.5 mmol) was added concurrently to a solution of 5-chloro-2,4-difluorobenzenesulfonyl chloride (2.60 g, 10.5 mmol) in acetonitrile (50 mL, 1000 mmol). The reaction mixture was stirred for 18 h then concentrated. The residue was dissolved in ethyl acetate (30 mL), washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified on automated silica gel chromatography (chloroform to 50% of 10% methanol in chloroform) to give 800 mg of the desired product as a yellow solid.

Aufarbeitung

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on automated silica gel chromatography (chloroform to 50% of 10% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-69c130f46a43405c8ab272fa1855e7ad
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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