1,2-Dichloroethane → HCID 136337161, Verbindung

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Reaktionsgleichung

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11](=[N:30][C:31]([O:33]CC)=O)[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH:10]=1)=[O:5])[CH3:2].ClCCCl>[Ti](Cl)(Cl)(Cl)Cl.CCO>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:30][C:31](=[O:33])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Titanium (IV) chloride (0.86 mL, 7.8 mmol) was added to a solution of 1-{ethoxycarbonylimino-[4-(naphthalen-1-yloxy)-phenylamino]methyl}-1H-pyrazole-4-carboxylic acid ethyl ester (0.74 g, 1.6 mmol) and DCE (10 mL), and the resulting mixture was heated to 90° C. for 16 h. The reaction mixture was cooled to room temperature and poured into 50 mL EtOH. The mixture was stirred for 30 min and the solid precipitate was collected by vacuum filtration (0.46 g, 69%). MS (ESI): mass calcd. for C24H18N4O4, 426.1; m/z found, 427.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.87 (s, 1H), 8.99 (s, 1H), 8.29 (s, 1H), 8.05 (d, J=7.5 Hz, 1H), 8.02 (d, J=8.3 Hz, 1H), 7.86 (d, J=8.3 Hz, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.70 (dd, J=8.9, 2.9 Hz, 1H), 7.64-7.60 (m, 1H), 7.60-7.53 (m, 2H), 7.39 (d, J=2.8 Hz, 1H), 7.23 (d, J=7.4 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
filtrationthe solid precipitate was collected by vacuum filtration (0.46 g, 69%)

Quellen und Nachweise

ORD-Eintrag: ord-b801f5e286044d34b07c043e15c3e475
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08937078B2

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