Triethylamine → 1-[4-(4-Ethoxyphenoxy)benzyl]-2-methylbenzimidazole

HRID 65089

Reaktionsgleichung

Reaktionsgleichung von HRID 65089
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH2:18]([O:20][C:21]1[CH:35]=[CH:34][C:24]([O:25][C:26]2[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=2)=[CH:23][CH:22]=1)[CH3:19]>C1(C)C=CC=CC=1>[CH2:18]([O:20][C:21]1[CH:35]=[CH:34][C:24]([O:25][C:26]2[CH:33]=[CH:32][C:29]([CH2:30][N:3]3[C:4]4[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=4[N:6]=[C:2]3[CH3:1])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1)[CH3:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 119842-MethylbenzimidazoleHCID 137303804-(4-Ethoxyphenoxy)benzyl chloride

Produkt 1

HCID 135634041-[4-(4-Ethoxyphenoxy)benzyl]-2-methylbenzimidazoleAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of toluene (20 ml), 2-methylbenzimidazole (0.55 g, 4.2 mmole), triethylamine (0.42 g, 4.2 mmole) and 4-(4-ethoxyphenoxy)benzyl chloride (1.00 g, 3.8 mmole) was heated under reflux for 5 hours and then cooled to room temperature. The resultant mixture was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 1-[4-(4-ethoxyphenoxy)benzyl]-2-methylbenzimidazole (1.20 g) as colorless liquid. nD26.0 1.5984.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. washThe resultant mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove toluene
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4d3582a376fb4abda8b517ac664f2d3e
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612323

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