Triethylamine → N-[2-[2-Cyanophenoxy]phenyl]-4-hexyloxybenzamide

HRID 1609269

Reaktionsgleichung

Reaktionsgleichung von HRID 1609269
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].C(N(CC)CC)C.[CH2:24]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CCOCC>[C:7]([C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[NH:1][C:35](=[O:36])[C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:39][CH:38]=1)#[N:8]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 170235Benzoyl chloride, 4-(hexyloxy)-HCID 200843882-(2-Aminophenoxy)benzonitrile

Produkt 1

HCID 20084541N-[2-[2-Cyanophenoxy]phenyl]-4-hexyloxybenzamideAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

In 20 ml of ether was dissolved 2.0 g of 2-(2-aminophenoxy)benzonitrile followed by addition of 2.04 g of triethylamine. Then, with ice-cooling and stirring, a solution of 2.67 g of 4-hexyloxybenzoyl chloride in 5 ml of ether was added dropwise. The mixture was further stirred at the same temperature for 1 hour. The reaction mixture was then washed with diluted hydrochloric acid and aqueous sodium hydrogen carbonate solution in that order, dried and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate-n-hexane as the eluent and the relevant fraction was crystallized from diisopropyl ether to give 3.05 g of the title compound as white crystals.

Aufarbeitung

  1. temperatureThen, with ice-cooling
  2. stirringThe mixture was further stirred at the same temperature for 1 hour
  3. washThe reaction mixture was then washed with diluted hydrochloric acid and aqueous sodium hydrogen carbonate solution in that order
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customthe relevant fraction was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5b022dcb1f1d4d9ba8c88d9364ccec6c
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05399703

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