Thionyl Chloride → 2-Chloro-5,7-difluorobenzo[D]thiazole

HRID 598528

Reaktionsgleichung

Reaktionsgleichung von HRID 598528
[F:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]2[S:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.S(Cl)([Cl:15])=O>CN(C)C=O>[Cl:15][C:8]1[S:9][C:5]2[C:4]([F:12])=[CH:3][C:2]([F:1])=[CH:11][C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 178505913HCID 178505913, Verbindung

Produkt 1

HCID 219857472-Chloro-5,7-difluorobenzo[D]thiazoleAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 2 g (9.841 mmol) 5,7-difluoro-benzothiazole-2-thiol in 10.7 mL (147.6 mmol) thionyl chloride was added drop wise 215 □L N,N-dimethylformamide at room temperature. The mixture was stirred at room temperature for 2 days. The solvent was removed in vacuo. The crude compound was purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 659 mg (32.6%) of the title compound as an off-white solid. MS(m/e): 205 (M+H+).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customThe crude compound was purified with flash column chromatography on silica eluting with a gradient
  3. customformed from n-heptane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9c787198f10e408e9aaa49a185464490
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897627B2

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