Pyridine → N-Acetyl-2-[4-(hexadecyloxy)phenoxy]-N-(2-pyridinylmethyl)acetamide

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Reaktionsgleichung

[CH2:1]([O:17][C:18]1[CH:35]=[CH:34][C:21]([O:22][CH2:23][C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:36](OC(=O)C)(=[O:38])[CH3:37].N1C=CC=CC=1>O>[C:36]([N:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:24](=[O:25])[CH2:23][O:22][C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:35][CH:34]=1)(=[O:38])[CH3:37]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 0.70 g of product from Example 88, 2.96 g of acetic anhydride, 0.027 g of 4-N,N-dimethylaminopyridine and 15 ml of pyridine is heated at 110° C. for 35 hours and at reflux temperature for 57 hours. The reaction is poured into water and extracted with methylene chloride. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 35% ethyl acetate/hexane) to give 0.366 g of product as light yellow crystals.

Aufarbeitung

temperatureat reflux temperature for 57 hours
extractionextracted with methylene chloride
washThe organic layer is washed with saturated sodium chloride
customdried
concentrationconcentrated in vacuo
customThe residue is purified by column chromatography (silica gel: 35% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-45f12bc8f7f64e418b7813bec199d7ea
Quelldatensatz: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05208247

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