N-Benzylidene-4-bromoaniline → N-(4-Bromophenyl)-N-(1-phenylethyl)amine

HRID 432324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432324
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:16][Li]>C1(C)C=CC=CC=1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:16])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 262176N-Benzylidene-4-bromoanilineHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 12174320N-(4-Bromophenyl)-N-(1-phenylethyl)amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a solution of N-(4-bromophenyl)-N-(1-phenylmethylidene)amine (1.0 g, 0.00385 mol) in toluene (30 mL) cooled to −78° C., a 1.4M solution of methyl lithium in diethyl ether (5.5 mL) was added dropwise keeping the temperature below −75° C. The solution was warmed up to −40° C. and stirred at this temperature under an atmosphere of nitrogen for 3 hours. The reaction mixture was quenched by a dropwise addition of water and the layers were separated. The organic phase was washed with brine (50 mL), dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(1-phenylethyl)amine (1.03 g, 0.00373 mol) as an off-white solid.

Aufarbeitung

  1. customthe temperature below −75° C
  2. customThe reaction mixture was quenched by a dropwise addition of water
  3. customthe layers were separated
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e499d1564ee44a958f9479b62bfb4acf
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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