4-Toluenesulfonyl chloride → 2-Tosyl-2,3-dihydropyridazine-3-carbonitrile

HRID 386600

Reaktionsgleichung

Reaktionsgleichung von HRID 386600
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].C[Si]([C:15]#[N:16])(C)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:1]2[CH:6]([C:15]#[N:16])[CH:5]=[CH:4][CH:3]=[N:2]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 9259PyridazineHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 136429372-Tosyl-2,3-dihydropyridazine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of pyridazine (1.807 mL, 24.98 mmol), aluminum chloride (0.010 g, 0.075 mmol) and trimethylsilyl cyanide (6.03 mL, 45.0 mmol) in DCM (30 mL) was stirred under a nitrogen atmosphere at 0° C. for 20 min. A solution of p-toluenesulfonyl chloride (8.19 g, 43.0 mmol) in DCM (60 mL) was added dropwise over 1 h. The reaction was warmed to room temperature, stirred for an additional 65 h and concentrated. The residue was treated with EtOH (50 mL) and the resulting solids were filtered to afford the title compound. HPLC/MS: 262.1 (M+1); Rt=2.51 min.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe residue was treated with EtOH (50 mL)
  3. filtrationthe resulting solids were filtered

Quellen und Nachweise

ORD-Eintrag
ord-b7169558c5f24a0398c503fd07f58ce4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372857B2

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