Thiophosgene → 3,5-Dichloro-2-isothiocyanatopyridine

HRID 1398863

Reaktionsgleichung

Reaktionsgleichung von HRID 1398863
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[C:7]([NH2:13])=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:5][C:6]1[C:7]([N:13]=[C:1]=[S:2])=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1

Komponenten

5

Edukt 2

HCID 10040ThiophosgeneHCID 778863,5-Dichloro-3-pyridylamine

Produkt 1

HCID 233404453,5-Dichloro-2-isothiocyanatopyridineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Versuchsvorschrift

Thiophosgene (21.9 ml, 288 mmol) was added dropwise to a stirred mixture of 3,5-dichloropyridin-2-amine (23.5 g, 144 mmol) in tetrahydrofuran (150 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. 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 purified by flash column chromatography on silica gel eluting with a 5-30% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (11.4 g, 55.6 mmol, 39%).

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. customThe residue was purified by flash column chromatography on silica gel eluting with a 5-30% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-baca3a2a9d6d47568444d9fe37d55cfc
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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