Benzyl Bromide → 2-Benzyloxymethyl-1-(3,5-dichloro-benzyl)-1H-imidazole

HRID 2101510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101510
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][OH:14].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:14][CH2:13][C:9]1[N:8]([CH2:7][C:6]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:4]([Cl:3])[CH:5]=2)[CH:12]=[CH:11][N:10]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 57801498[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol

Produkt 1

HCID 119512412-Benzyloxymethyl-1-(3,5-dichloro-benzyl)-1H-imidazoleAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To NaH in DMF, was added [1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-methanol (see Example 1) in DMF. The reaction mixture was stirred at 40° C. for 30 min and benzyl bromide was dropwise added. The reaction mixture was stirred at 40° C. for another 3 h. The mixture was diluted with EtOAc and washed with water, 1N HCl and saturated NaHCO3. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 98:2 as an eluent to afford the title compound (7 mg, 5%); MS m/z 347 [C18H16Cl2N2O+H]+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 40° C. for another 3 h
  2. washwashed with water, 1N HCl and saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-3046409271b84e10b6d14775e033c287
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572921B2

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