Ethylene Glycol → N-Benzyl-3,5-dimethylaniline

HRID 2179181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179181
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[CH2:9]([NH:16][C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

8

Edukt 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzene

Produkt 1

HCID 10176701N-Benzyl-3,5-dimethylanilineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 5-iodo-m-xylene (144 μl, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.5) afforded 5-(N-benzyl)amino-m-xylene (177 mg, 84% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144-1157.

Quellen und Nachweise

ORD-Eintrag
ord-aa48b41f7e304134bc64a94bed7bb17a
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067955B2

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