4-Benzyloxyaniline → 3-(4-Benzyloxyphenyl)-1-(2,2-dimethoxyethyl)-1-(4-phenoxyphenyl)urea

HRID 723334Notizen

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17].[CH3:28][O:29][CH:30]([O:46][CH3:47])[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:35][CH:34]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:16](=[O:17])[N:32]([CH2:31][CH:30]([O:46][CH3:47])[O:29][CH3:28])[C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:35][CH:34]=2)=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A solution of 4-benzyloxyaniline (199 mg) in dimethylformamide (1 ml) was added dropwise to a solution of carbonyldiimidazole (162 mg) in dimethylformamide (1 ml) at 0° C. After a reaction time at 0° C. of 10 minutes, the reaction was allowed to continue at room temperature for 20 minutes. Then (2,2-dimethoxyethyl)-(4-phenoxyphenyl)amine (273 mg) was added, and the mixture was heated at 80° C. for 1.5 hours. Cooling was followed by dilution with water and extraction with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 498.58 (C30H30N2O5); MS (ESI): 499 ([M+H]+), was obtained in this way.

Aufarbeitung

waitto continue at room temperature for 20 minutes
temperatureCooling
extractionwas followed by dilution with water and extraction with ethyl acetate
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customMS (ESI): 499 ([M+H]+), was obtained in this way

Quellen und Nachweise

ORD-Eintrag: ord-0f11f72f476a4292a628fef156f83830
Quelldatensatz: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07141561B2

Notizen zur Reaktion

Wird geladen…