Azobisisobutyronitrile → Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 646903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646903
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:25])[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[CH:9]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22954042Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Produkt 1

HCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylateAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid methyl ester (0.43 g, 1.6 mmol) (as prepared in the previous step) in CCl4 (10 mL) was added NBS (0.30 g, 1.7 mmol) and AIBN (cat) and the mixture heated at 60° C. for 4 h. The reaction was diluted with EtOAc (30 ml) and washed with satd NaHCO3 (2×30 mL) and brine (30 mL) and the organic layer concentrated. The title compound was eluted from a 20-g SPE cartridge (silica) with 50% EtOAc/hexane to give 0.40 g (71%) of a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C11H19BrN2O3Si, 335.0/337.0 (M+H), found 335.0/337.0.

Aufarbeitung

  1. washwashed with satd NaHCO3 (2×30 mL) and brine (30 mL)
  2. concentrationthe organic layer concentrated
  3. washThe title compound was eluted from a 20-g SPE cartridge (silica) with 50% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a52b9d53558d4bab81687be988eab0ed
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705042B2

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