5-Nitrobenzimidazole → methyl (E)-11-[2-(5-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

HRID 358994

Reaktionsgleichung

Reaktionsgleichung von HRID 358994
Cl[CH2:2]/[CH:3]=[C:4]1/[C:5]2[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:6]=2[O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]/1=2.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]2[N:30]=[CH:31][NH:32][C:28]=2[CH:27]=1)([O-:25])=[O:24]>>[N+:23]([C:26]1[CH:34]=[CH:33][C:29]2[N:30]([CH2:2]/[CH:3]=[C:4]3/[C:5]4[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:6]=4[O:7][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]/3=4)[CH:31]=[N:32][C:28]=2[CH:27]=1)([O-:25])=[O:24].[N+:23]([C:26]1[CH:34]=[CH:33][C:29]2[N:30]=[CH:31][N:32]([CH2:2]/[CH:3]=[C:4]3/[C:5]4[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:6]=4[O:7][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]/3=4)[C:28]=2[CH:27]=1)([O-:25])=[O:24]

Komponenten

4

Edukt 2

HCID 71955-NitrobenzimidazoleHCID 10448388Methyl (E)-11-(2-chloroethylidene)-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Produkt 2

HCID 10094839methyl (E)-11-[2-(5-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylateHCID 11744007methyl (E)-11-[2-(6-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Versuchsvorschrift

Compound h, 2.0 g, and 5.2 g of 5-nitrobenzimidazole were treated in a manner similar to Example 23 to give a 1:1 mixture of Compounds E-55a and E-56a. The mixture was separated and purified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1) to give 1.1 g of methyl (E)-11-[2-(5-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound E-55a) and 0.7 g of methyl (E)-11-[2-(6-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound E-56a).

Aufarbeitung

  1. customto give
  2. additiona 1:1 mixture of Compounds E-55a and E-56a
  3. customThe mixture was separated
  4. custompurified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f724cae73b174b24b1bb97b626161d90
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04999363

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