Sodium hydride → 3-[3-Amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

HRID 546572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546572
[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]2=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[H-].[Na+].[Cl:24][C:25]1[CH:30]=[C:29]([CH2:31]Cl)[CH:28]=[CH:27][N:26]=1>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:19])([CH3:20])[N:15]([CH2:31][C:29]3[CH:28]=[CH:27][N:26]=[C:25]([Cl:24])[CH:30]=3)[C:14]2=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:10])([F:11])[F:12]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 576259883-[3-Amino-4-(trifluoromethoxy)-phenyl]-5,5-dimethylimidazolidine-2,4-dione

Produkt 1

HCID 576260063-[3-Amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dioneAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 4.9 g of 3-[3-amino-4-(trifluoromethoxy)-phenyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage b) below in 200 mL of dimethylformamide are added, under argon, 0.68 g of 60% sodium hydride and stirring is continued for 20 minutes at room temperature. To this solution are added 2.85 g of 2-chloro-4-chloromethylpyridine obtained in stage b) of Example 3 dissolved in 20 mL of dimethylformamide, and the reaction mixture is then heated at 70° C. for 3.5 hours and then poured into 500 mL of ice-water and extracted with three times 300 mL of ethyl acetate. The combined organic phases are dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is taken up in 500 mL of diethyl ether, washed with water, dried over magnesium sulphate, filtered and concentrated under vacuum to give 6.8 g of 3-[3-amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows:

Aufarbeitung

  1. extractionextracted with three times 300 mL of ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dd1fa398b6d74132be7a686f2b10d9ab
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935819B2

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