(4-Aminophenoxy)benzene → (2,2-Dimethoxyethyl)-(4-phenoxyphenyl)amine

HRID 723327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723327
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC>CN(C)C=O>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH:12][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 8764(4-Aminophenoxy)benzeneHCID 816722-Bromo-1,1-dimethoxyethaneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine

Produkt 1

HCID 21873313(2,2-Dimethoxyethyl)-(4-phenoxyphenyl)amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 4-phenoxyaniline (915 mg) in dimethylformamide (5 ml) was mixed with bromoacetaldehyde dimethyl acetal (1.1 ml) and BEMP (1.9 ml). The reaction mixture was shaken at 100° C. for 16 hours. Volatiles were removed and the residue was purified by chromatography on silica gel (eluent: dichloromethane/hexane 1:2, later 1:1 with in each case 1% v/v 7N ammonia solution in methanol). The product with the molecular weight of 273.33 (C16H19NO3); MS (ESI): 274 ([M+H]+), was obtained in this way.

Aufarbeitung

  1. customVolatiles were removed
  2. customthe residue was purified by chromatography on silica gel (eluent
  3. customMS (ESI): 274 ([M+H]+), was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-1e2893f94d5746589681acb1a983916d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141561B2

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