Sodium Iodide → ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoate

HRID 659934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659934
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.Br[CH2:7][CH2:8][O:9][C:10]1[C:11]([Cl:22])=[C:12]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[Cl:22][C:11]1[C:10]([O:9][CH2:8][CH2:7][N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[C:20]([Cl:21])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl:22][C:11]1[C:10]([O:9][CH2:8][CH2:7][N:2]2[NH:3][N:4]=[CH:5][NH:1]2)=[C:20]([Cl:21])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15029235Ethyl 3-(2-bromoethoxy)-2,4-dichlorobenzoateHCID 178418441HCID 178418441, Verbindung

Produkt 2

HCID 57437285ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoateHCID 66734875ethyl 2,4-dichloro-3-[2-(1H-tetrazol-2-yl)ethoxy]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1H-tetrazol (0.45 g) and ethyl 3-(2-bromoethoxy)-2,4-dichlorobenzoate (2.00 g) were suspended in DMF (15 ml), potassium carbonate (1.21 g) and sodium iodide (0.04 g) were added thereto and the mixture was stirred at 80° C. for 3 hours. After the reaction, cool water was added, extracted with ethyl acetate (100 ml) and dried over anhydrous magnesium sulfate. The residue obtained by distilling off ethyl acetate was purified with silica gel column chromatography (elution solvent; ethyl acetate: hexane=1:1) to obtain the desired ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoate (0.88 g) and ethyl 2,4-dichloro-3-[2-(1H-tetrazol-2-yl)ethoxy]benzoate (0.99 g).

Aufarbeitung

  1. customAfter the reaction
  2. additionwas added
  3. extractionextracted with ethyl acetate (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off ethyl acetate
  7. customwas purified with silica gel column chromatography (elution solvent; ethyl acetate: hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-21b447b0c93749c0a26ac60350a7749f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084398B2

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