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Triethylamine → HCID 20222380, Verbindung

HRID 1285379
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1285379
[NH2:1][CH:2]([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>C(#N)C>[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:1][CH:2]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 201311651-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

Produkt 1

HCID 20222380HCID 20222380, VerbindungAusbeute 3,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (1.70 g, 0.0065M) in dry acetonitrile (10 ml) containing triethylamine (0.5 ml) was treated with 4-methoxybenzyl chloride (1.12 g, 0.0072M) and heated under reflux for 18 hours under a stream of dry nitrogen. The solvent was evaporated off under reduced pressure and the residue was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and dried (MgSO4). The solvent was evaporated off under reduced pressure to give the crude product as an oil which was further purified by chromatography (silica gel), 10% ethanol in chloroform) to give N-[(4-methoxyphenyl)methyl]-α-[[(4-methoxyphenyl)methoxy]methyl]-1H-imidazole-1-ethanamine (0.09 g) as a pale yellow oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 18 hours under a stream of dry nitrogen
  3. customThe solvent was evaporated off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated off under reduced pressure
  8. customto give the crude product as an oil which
  9. customwas further purified by chromatography (silica gel), 10% ethanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-ba1e32c161a247829dc4cc6c3f995fe7
Quelldatensatz
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04567189

Notizen zur Reaktion

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