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Ammonium Chloride → 2[2-(2-Methylphenoxymethyl)-benzoyl]-imidazole

HRID 567114
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 567114
C(OC(OCC)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)C.C([Li])CCC.[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:25](N1CCCC1)=[O:26].[Cl-].[NH4+]>O1CCCC1.CO>[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:25]([C:6]1[NH:5][CH:9]=[CH:8][N:7]=1)=[O:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 38495351-(diethoxymethyl)-1H-imidazoleHCID 21264588HCID 21264588, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 153461052[2-(2-Methylphenoxymethyl)-benzoyl]-imidazoleAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

At −40° C., 6.9 g (0.0405 mol) of N-diethoxymethylimidazole (J. Org. Chem. Vol. 45, No. 20, 1980, page 4040) in 40 ml of tetrahydrofuran are mixed with 11.3 g (0.0405 mol) of 23% pure n-butyllithium, and the mixture is stirred at −60° C. for one hour. At −40° C., 6 g (0.0203 mol) of N-[2-(2-methylphenoxymethyl)-benzoyl]-pyrrolidine are added, and the mixture is stirred for 30 minutes without any further cooling, on which the reaction mixture warms to 20° C. 5 g of ammonium chloride and 50 ml of methanol are added, and the mixture is heated at reflux for 15 minutes. The volatile components are distilled off under reduced pressure and the residue is admixed with water and extracted with ethyl acetate. The organic phase is dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate. 3.79 g (63.8% of theory) of 2[2-(2-methylphenoxymethyl)-benzoyl]-imidazole are obtained.

Aufarbeitung

  1. customAt −40° C.
  2. stirringthe mixture is stirred for 30 minutes without any further cooling, on which the reaction mixture
  3. customwarms to 20° C
  4. temperaturethe mixture is heated
  5. temperatureat reflux for 15 minutes
  6. distillationThe volatile components are distilled off under reduced pressure
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is dried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bfb1cab7d81e4942a10ae14ffd0fdfd0
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06177459B1

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