Triethylamine → HCID 66812315, Verbindung

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Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9](Cl)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:21][CH2:20][CH2:19][N:18]([CH3:22])[CH3:17])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 3-(4-chloro-3-nitro-phenyl)-acrylic acid methyl ester (Ia, 0.658 g, 2.72 mmol), N,N-dimethylethylenediamine (0.90 mL, 8.20 mmol) and triethylamine (1.2 mL, 8.6 mmol) in dioxane (20 mL) was heated at 80° C. for 5 h. The solution was evaporated and the residue was added DCM and aqueous Na2CO3. The DCM (×3) extracts were concentrated and the residue was added EtOAc-hexane. The resulting red solid was filtered to give the titled compound (0.672 g, 84.2%). HPLC purity at 254 nm: 99.2%, tR=1.59 min. LCMS (ESI) m/z: 294 ([M+H]+). 1H NMR (CDCl3+CD3OD) δ 8.21 (1H, d, J=2.1 Hz), 7.56 (1H, dd, J=9.0, 2.1 Hz), 7.48 (1H, d, J=16.0 Hz), 6.81 (1H, d, J=9.0 Hz), 6.20 (1H, d, J=15.9 Hz), 3.70 (3H, s), 3.34 (2H, t, J=6.5 Hz), 2.56 (2H, t, J=6.4 Hz), 2.23 (6H, s); 13C NMR (CDCl3+CD3OD) δ 167.3, 145.4, 142.6, 134.0, 131.1, 127.1, 121.3, 114.8, 114.0, 56.7, 51.1, 44.6, 40.1.

Aufarbeitung

customThe solution was evaporated
additionthe residue was added DCM and aqueous Na2CO3
concentrationThe DCM (×3) extracts were concentrated
additionthe residue was added EtOAc-hexane
filtrationThe resulting red solid was filtered

Quellen und Nachweise

ORD-Eintrag: ord-3781a3f897c641b2aef326b6b8eed684
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08143282B2

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