Thiophosgene → 5-Isothiocyanato-2-methoxy-4,6-dimethylpyrimidine

HRID 1628513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628513
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([NH2:14])=[C:9]([CH3:15])[N:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:14]([C:10]1[C:9]([CH3:15])=[N:8][C:7]([O:6][CH3:5])=[N:12][C:11]=1[CH3:13])=[C:1]=[S:2]

Komponenten

5

Edukt 2

HCID 10040ThiophosgeneHCID 687393852-Methoxy-4,6-dimethylpyrimidin-5-amine

Produkt 1

HCID 866328935-Isothiocyanato-2-methoxy-4,6-dimethylpyrimidineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Thiophosgene (1.8 mL, 23.6 mmol) was added dropwise to a stirred mixture of 2-methoxy-4,6-dimethylpyrimidin-5-amine (2.82 g, 18.4 mmol) in tetrahydrofuran (25 mL) and saturated aqueous sodium hydrogen carbonate (25 mL) at 0° C., and the mixture was stirred at 0° C. for 40 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 diisopropyl ether/n-hexane to give the title compound as a pale yellow powder (3.16 g, 16.2 mmol, 88%).

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 diisopropyl ether/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e736bd3fcc62484c91a6ac605e8f2559
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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