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

HRID 1692357Notes

Reaction equation

HRID 1692357 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

HCID 594365565-chloro-2,4-difluoro-N-pyridazin-3-ylbenzenesulfonamideYield 24.9%

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1832696f37b2473485aafc3f1057d48d
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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