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Acetic Acid → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine

HRID 15705
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 15705
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[CH3:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[NH2:22].C(O)(=O)C.[BH4-].[Na+]>C(O)C.C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH2:12][NH:22][C:21]2[CH:23]=[C:24]([CH3:26])[CH:25]=[C:19]([CH3:18])[CH:20]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 79493,5-DimethylanilineHCID 4311764Sodium borohydrideHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde

Produkt 1

HCID 131727120N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amineAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (15.0 mmol) in ethanol (44.6 mL) were added dropwise 3,5-dimethylaniline (15.8 mmol) and acetic acid (1.5 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature. After disappearance of the aldehyde was confirmed by gas chromatography, sodium borohydride (19.5 mmol) was added to the solution and reacted at room temperature for 3 hrs. Water and toluene were then added to the reaction mixture. The organic layer was dried and concentrated. The obtained oily substance was purified by silica gel column chromatography to give N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine (4.88 g, yield 73.3%) as a yellow oily substance.

Aufarbeitung

  1. additionwas added to the solution
  2. customreacted at room temperature for 3 hrs
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe obtained oily substance was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3e24f844693c410390771f2533932470
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07732643B2

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