Ammonia → 3,5-Dimethylbenzonitrile

HRID 1243120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243120
[C-]#N.[K+].C[NH:5][CH2:6][CH2:7]NC.BrC1[CH:12]=[C:13]([CH3:18])[CH:14]=[C:15]([CH3:17])[CH:16]=1.CCCCCCCCCCCC.N>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[CH3:18][C:13]1[CH:12]=[C:7]([CH:16]=[C:15]([CH3:17])[CH:14]=1)[C:6]#[N:5]

Komponenten

9

Edukt 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 8182DodecaneHCID 9032Potassium CyanideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Produkt 1

HCID 897183,5-DimethylbenzonitrileAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 20 mol %), KCN (78 mg, 1.20 mmol), evacuated, backfilled with Ar. N,N′-Dimethylethylenediamine (21.5 μL, 0.202 mmol, 20 mol %), 5-bromo-m-xylene (136 μL, 1.00 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. Dodecane (internal GC standard, 230 μL), ethyl acetate (2 mL), and 30% aq ammonia (1 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 15% yield of 3,5-dimethylbenzonitrile.

Aufarbeitung

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve

Quellen und Nachweise

ORD-Eintrag
ord-68572722fd6f496ca81a477b15542658
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115784B2

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