Iodoethane → HCID 67160209, Verbindung

HRID 601632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601632
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[NH:14][N:13]=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18](I)[CH3:19]>C1COCC1.C(OC(=O)C)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[N:12][N:13]([CH2:18][CH3:19])[N:14]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178453348HCID 178453348, Verbindung

Produkt 1

HCID 67160209HCID 67160209, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of [2-(1H-Tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester (EP 449523) (1.0 g, 4.69 mmol) in dry THF (20 ml) is treated with a 60% dispersion of sodium hydride in mineral. oil (0.19 g, 4.69 mmol) and stirred at ambient temperature for 10 minutes. Ethyliodide (0.375 ml, 4.69 mmol) is added and the reaction mixture is heated at reflux for 7 hours, then diluted with ethylacetate and filtered. The filtrate is evaporated and the residue purified by flash silica chromatography (elution 3:2 hexanelethylacetate) to afford [2-(2-Ethyl-2H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, which elutes first, and the titled compound, [2-(1-Ethyl-1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, which elutes next.

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 7 hours
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue purified by flash silica chromatography (elution 3:2 hexanelethylacetate)

Quellen und Nachweise

ORD-Eintrag
ord-c9bf2c3934c041ddb443f136780d0504
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902375B2

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