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2-Nitroimidazole → 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514617
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 514617
Br[CH2:2][C:3]1([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.[N+:20]([C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)([O-:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.O>[O:12]([CH2:11][C:3]1([CH2:2][N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[N+:20]([O-:22])=[O:21])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 903004745-Bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

Produkt 1

HCID 903005825-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

578 mg (1.64 mmol equivalents) of 5-bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane was dissolved in 10 mL of dimethylformamide, 186 mg (1.64 mmol equivalents) of 2-nitroimidazole and 680 mg (4.92 mmol equivalents) of potassium carbonate were added thereto, and the mixture was heated to 100° C. for 18 hours. After completion of the reaction, the reaction liquid was cooled to room temperature (25° C.), a saturated aqueous solution of ammonium chloride and water were added thereto, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1) to give 363 mg (0.942 mmol equivalents) of 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. temperaturewas cooled to room temperature (25° C.)
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationsubsequently concentrated under vacuum
  8. customthe obtained crude product
  9. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-39ac64494d3d4088a937819bd9bda618
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09107964B2

Notizen zur Reaktion

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