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

HRID 1402062

반응식

HRID 1402062 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-399920cb9fc04d8385b6711978db577e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907101B2

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