2-Amino-1-butanol → 1,3-Bis[(4-ethyl-4,5,-dihydro-2-oxazolyl)methyl]benzene

HRID 132974

Reaktionsgleichung

[C:1]1([CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.N[CH:14]([CH2:17][CH3:18])[CH2:15][OH:16]>CC1C=CC=CC=1C.O.O.O.O.[N+]([O-])([O-])=O.[Cd+2].[N+]([O-])([O-])=O>[CH2:17]([CH:14]1[CH2:15][O:16][C:11]([CH2:10][C:1]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]3[O:16][CH2:15][CH:14]([CH2:17][CH3:18])[N:9]=3)[CH:2]=2)=[N:12]1)[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

In a one liter four-necked round-bottom flask equipped with a condenser, N2 inlet/outlet, magnetic stirrer, and thermometer, was charged with 52.65 g of 1,3-phenylene-diacetonitrile (0.337 mol, Aldrich), 78.13 g of 2-amino-1-butanol (0.876 mol, Aldrich), and 3.38 g of cadmium nitrate tetrahydrate (0.011 mol, Aldrich) in 300 mL of o-xylene. The mixture was heated to 130° C. and the reaction was run for 72 hours. The cooled mixture was washed with de-ionized water (2×200 mL). The organic layer was dried over sodium sulfate and acidic alumina gel. After removal of solvent in vacuo, 67.21 g of an amber liquid resin was obtained in a yield of 67%. The viscosity of this resin at room temperature is 250 mPa.·. 1H NMR (CDCl3, 400 MHz): δ 7.11-7.19 (m, 4H), 4.20 (t, 2H), 3.91-3.97 (m, 2H), 3.77 (t, 2H), 3.52 (s, 4H), 1.53-1.61 (m, 2H), 1.40-1.47 (m, 2H), 0.86 (t, 6H).

Aufarbeitung

customIn a one liter four-necked round-bottom flask equipped with a condenser, N2 inlet/outlet, magnetic stirrer
washThe cooled mixture was washed with de-ionized water (2×200 mL)
dry with materialThe organic layer was dried over sodium sulfate and acidic alumina gel
customAfter removal of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-fb9b9f551bd34ee5a3477b6d658efbf8
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07390430B2

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