3-Bromobenzyl bromide → 1-Bromo-3-[2,2-bis(ethoxycarbonyl)-2-(p-toluoylamino)ethyl]benzene

HRID 890646

Reaktionsgleichung

Reaktionsgleichung von HRID 890646
[O-]CC.[Na+].C(O)C.[C:8]1([CH3:28])[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15])=[CH:10][CH:9]=1.[Br:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br>C(O)C>[Br:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:32]([CH2:33][C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH3:28])=[CH:9][CH:10]=2)=[O:15])[CH:31]=1

Komponenten

5

Edukt 3

HCID 699793-Bromobenzyl bromideHCID 17447783Diethyl p-toluoylaminomalonateHCID 23706232Ethanol sodium ethoxide

Produkt 1

HCID 218667981-Bromo-3-[2,2-bis(ethoxycarbonyl)-2-(p-toluoylamino)ethyl]benzeneAusbeute 107,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 100 ml of dry ethanol, 21.45 g of 20% sodium ethoxide-ethanol solution and 17.61 g of diethyl p-toluoylaminomalonate were added and stirred for 30 minutes at room temperature under argon atmosphere. After 15.00 g of 3-bromobenzyl bromide was added dropwise, the reaction solution was stirred for 8 hours at 55° C. and then concentrated. To the residue was added water, and extracted with ethyl acetate. The organic.layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to provide 29.82 g of the objective compound as yellow oil.

Aufarbeitung

  1. stirringthe reaction solution was stirred for 8 hours at 55° C.
  2. concentrationconcentrated
  3. additionTo the residue was added water
  4. extractionextracted with ethyl acetate
  5. washThe organic.layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-18e51c0b0b6948b1bfe908ff01fee0d6
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998412B2

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