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Potassium Carbonate → 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazole

HRID 1591377
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1591377
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C1(C)C=CC=CC=1.O>[CH2:1]([C:5]1[N:6]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 685274-Bromobenzyl bromideHCID 178418251HCID 178418251, Verbindung

Produkt 1

HCID 99505572-n-Butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazoleAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.6 m=111.9 g), p-bromobenzylbromide (0.6 m=153.02 g), anhydrous potassium carbonate (0.75 m=103.5 g), and dry N,N-dimethylacetamide (900 mL) was stirred at room temperature for 4 hours. The mixture was diluted with 1.2L of toluene and 1.8L of water. After mixing for half an hour, the layers were separated. The organic layer was washed two more times with 900 mL portions of water, then dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated. The residual oil was pumped overnight to a weight of 191.71 g (89.9% yield).

Aufarbeitung

  1. additionAfter mixing for half an hour
  2. customthe layers were separated
  3. washThe organic layer was washed two more times with 900 mL portions of water
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated
  7. waitThe residual oil was pumped overnight to a weight of 191.71 g (89.9% yield)

Quellen und Nachweise

ORD-Eintrag
ord-736203f0521443fc931ef38db480a950
Quelldatensatz
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05206374

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