Thiophosgene → 5-Isothiocyanato-2-methoxy-4-methylpyridine

HRID 1398857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398857
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[CH:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:10]1[C:9]([CH3:14])=[CH:8][C:7]([O:6][CH3:5])=[N:12][CH:11]=1)=[C:1]=[S:2]

Komponenten

5

Edukt 2

HCID 10040ThiophosgeneHCID 2431706-Methoxy-4-methylpyridin-3-amine

Produkt 1

HCID 866328845-Isothiocyanato-2-methoxy-4-methylpyridineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Thiophosgene (8.9 mL, 120 mmol) was added dropwise to a stirred mixture of 6-methoxy-4-methylpyridin-3-amine (13.8 g, 99.8 mmol) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at 0° C. for 2 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 washed with n-hexane to give the title compound as a colorless powder (10.6 g, 58.8 mmol, 59%).

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-d17bc03c4b95426fba488b1b021ca0ff
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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