Thiophosgene → 5-Isothiocyanato-4,6-dimethoxy-2-methylpyrimidine

HRID 1628508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628508
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[C:12]([NH2:13])=[C:11]([O:14][CH3:15])[N:10]=[C:9]([CH3:16])[N:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:12]1[C:7]([O:6][CH3:5])=[N:8][C:9]([CH3:16])=[N:10][C:11]=1[O:14][CH3:15])=[C:1]=[S:2]

Komponenten

5

Edukt 2

HCID 10040ThiophosgeneHCID 212392004,6-Dimethoxy-2-methylpyrimidin-5-amine

Produkt 1

HCID 866328895-Isothiocyanato-4,6-dimethoxy-2-methylpyrimidineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Thiophosgene (7.7 mL, 101 mmol) was added dropwise to a stirred mixture of 4,6-dimethoxy-2-methylpyrimidin-5-amine (14.2 g, 84.3 mmol) in tetrahydrofuran (110 mL) and saturated aqueous sodium hydrogen carbonate (110 mL) at 0° C., and the mixture was stirred at 0° C. for 1 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 brown powder (12.5 g, 59.0 mmol, 70%).

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-4aedd531a78a406ab310cca013b72211
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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