Reaktionsgleichung
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N+:13]([O-:15])[CH3:14])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1.C(OCC)(=O)C.CCCCCC>C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[O:15][N:13]([CH3:14])[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)([CH2:7][N:8]3[CH:12]=[CH:11][N:10]=[CH:9]3)[CH2:22]2)=[CH:19][CH:18]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 7.60 g (0.037 mol) of 1-(2-furanyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide (4) and 7.70 g (0.056 mol) of 4-chlorostyrene in 400 ml of toluene is refluxed for 48 hours under a nitrogen atmosphere. Upon cooling to ambient temperature, the crude cis- and trans-diastereomeric mixture of compound 6 (R=C6H4Cl--4) is concentrated in vacuo and flash-chromatographed on neutral silica gel using a 98:2 by volume mixture of chloroform and methanol to give 1.30 g (10%) of isomer A, melting point 99°-101° C. (ethyl acetate-hexane, 1:1 by volume). Anal. Calcd. for C18H18ClN3O2 : C, 62.88; H, 5.28; Cl, 10.31; N, 12.22 Found: C, 62.90; H, 5.39; Cl, 10.44; N, 12,13. Isomer B (1.10 g, 8.5%) has a melting point of 131°-133° C. (ethyl acetate-hexane, 1:1 by volume). Anal. Calcd. for C18H18ClN3O2 : C, 62.88; H, 5.28; Cl, 10.31; N, 12.22. Found: C, 62.82; H, 5.28; Cl, 10.46; N, 12.12.
Aufarbeitung
- concentrationis concentrated in vacuo
- customflash-chromatographed on neutral silica gel using a 98:2
- additionby volume mixture of chloroform and methanol
- customto give 1.30 g (10%) of isomer A, melting point 99°-101° C. (ethyl acetate-hexane, 1:1 by volume)
Quellen und Nachweise
- ORD-Eintrag
- ord-1c2353670c7b4a3a980103fc44100eef
- Quelldatensatz
- uspto-grants-1988_09
- Patentnummer
- US04769469
Verknüpfte Notizen
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