Dimethylformamide → 5-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole

HRID 538989

Reaktionsgleichung

Reaktionsgleichung von HRID 538989
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.CN(C=O)C.[H-].[Na+].Cl[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:12]=2)=[CH:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 469487345-(4-Bromophenyl)-1H-1,2,4-triazole

Produkt 2

HCID 595259995-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazoleAusbeute 186 %HCID 595262653-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 5-(4-bromophenyl)-1H-1,2,4-triazole (5.40 g, 24.1 mmol) in DMF (48.2 mL, 24.1 mmol) at 0° C. was carefully added NaH (1.16 g, 28.9 mmol). The resultant mixture was stirred for 30 minutes prior to the addition of (2-(chloromethoxy)ethyl)trimethylsilane (6.38 mL, 36.2 mmol). The reaction mixture was stirred 0° C. for 15 minutes before removal of the ice bath and the mixture was allowed to warm to ambient temperature stirring for 2 hours. The reaction mixture was diluted with H2O (150 mL) and extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to provide 10.09 g as a pale yellow oil which solidified upon standing. Purification by normal phase chromatography on silica eluting with 0-50% EtOAc/Hexanes provided 3-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole and 5-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (7.94 g, 93%) as a mixture of two regioisomers. LCMS (APCI+) m/z 354, 356 [M+H]+.

Aufarbeitung

  1. customat 0° C.
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide 10.09 g as a pale yellow oil which
  8. customPurification by normal phase chromatography on silica eluting with 0-50% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-cdbb848719844e6983b1b90cc5e4056f
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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