Thiophosgene → 1,5-Dichloro-2-isothiocyanato-3-methylbenzene

HRID 1628503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628503
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([CH3:14])[C:7]=1[NH2:8]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([CH3:14])[C:7]=1[N:8]=[C:1]=[S:2]

Komponenten

5

Edukt 2

HCID 10040ThiophosgeneHCID 12682872,4-Dichloro-6-methylaniline

Produkt 1

HCID 27360131,5-Dichloro-2-isothiocyanato-3-methylbenzeneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Versuchsvorschrift

Thiophosgene (17.0 g, 148 mmol) was added dropwise to a stirred mixture of 2,4-dichloro-6-methylaniline (20.0 g, 114 mmol) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (100 mL) at 0° C., and the mixture was stirred at room temperature for 90 minutes. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give the title compound as a colorless powder (14.4 g, 66.0 mmol, 58%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-08d23939953b4891af48b607a722e0b9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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