Iodoethane → HCID 72187885, Verbindung

HRID 515164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515164
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[OH:24])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH3:33]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[O:24][CH2:32][CH3:33])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6340Iodoethane3×HCID 11430Potassium CarbonateHCID 86699734HCID 86699734, Verbindung

Produkt 1

HCID 72187885HCID 72187885, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of N-[(4-chlorophenyl)-methyl]-2-hydroxy-6-methyl-4-morpholin-4-yl-benzamide (0.2 g, 0.56 mmol) in acetone (5 ml) are added potassium carbonate (0.092 g, 0.66 mmol) and ethyl iodide (0.066 ml, 0.83 mmol). The reaction mixture is stirred at 50° C. for 1 h. Additional ethyl iodide (0.22 ml, 2.77 mmol) is added and heating is continued for another 2 h. Additional ethyl iodide (0.22 ml, 2.77 mmol) is then added and the reaction mixture is stirred for 15 h. After completion of reaction, the solution is filtered through a pad of celite and concentrated to obtain the crude product, which is purified by column chromatography (silica gel, 15% ethyl acetate/hexan) yielding N-[(4-chlorophenyl)-methyl]-2-ethoxy-6-methyl-4-morpholin-4-yl-benzamide (example 11) (0.12 g, 0.3 mmol, 56%). [M+H]+ 389.2.

Aufarbeitung

  1. temperatureheating
  2. waitis continued for another 2 h
  3. stirringthe reaction mixture is stirred for 15 h
  4. customAfter completion of reaction
  5. filtrationthe solution is filtered through a pad of celite
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customis purified by column chromatography (silica gel, 15% ethyl acetate/hexan)

Quellen und Nachweise

ORD-Eintrag
ord-7e755d4f9ea04846bc00aa0c354651c8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108936B2

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