1,5-Dibromopentane → 1-(5-Bromo-pentyl)-2-methyl-4,5-diphenyl-1H-imidazole

HRID 1351012

Reaktionsgleichung

Reaktionsgleichung von HRID 1351012
[CH3:1][C:2]1[NH:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[H-].[Na+]>CN(C=O)C>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:6]1[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=[C:2]1[CH3:1]

Komponenten

5

Edukt 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 2366964,5-Diphenyl-2-methylimidazole

Produkt 1

HCID 185375251-(5-Bromo-pentyl)-2-methyl-4,5-diphenyl-1H-imidazoleAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(Scheme 2 (E)) To a solution of 2-Methyl-4,5-diphenyl-1H-imidazole (2.0 g, 8.5 mmol) and 1,5-dibromopentane (3.01 g, 12.7 mmol) in DMF (100 mL) was added NaH (60% in mineral oil, 0.50 g, 12.7 mmol). The resulting mixture was stirred at rt for 1 hour, quenched by addition of water, extracted by CH2Cl2, washed by water, and then was dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: EtOAc/Hexanes). This compound was obtained as a pale yellow oil (2.2 g, 5.7 mmol, 67% yield): 1H NMR (DMSO): δ1.20 (m, 2H), 1.47 (m, 2H), 1.64 (m, 2H), 2.41 (s, 3H), 3.45 (t, 2H), 3.72 (t, 2H), 7.16 (m, 3H), 7.31 (m, 4H), 7.55 (t, 3H). Mass Spec: 384.57 (MH+).

Aufarbeitung

  1. customquenched by addition of water
  2. extractionextracted by CH2Cl2
  3. washwashed by water
  4. dry with materialwas dried over MgSO4
  5. filtrationAfter filtration and concentration in vacuo
  6. customthe residue was purified by flash chromatography (SiO2: EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cf392448696a4f54980430c1d06b376f
Quelldatensatz
uspto-grants-2007_05
Patentnummer
USRE039634E1

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