Reaction equation
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]Participants
4
Reactant 2
Product 2
Procedure
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).
Workup
- customto give
- additiona 1:1 mixture of Compounds E-55a and E-56a
- customThe mixture was separated
- custompurified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1)
Sources & evidence
- ORD record
- ord-f724cae73b174b24b1bb97b626161d90
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04999363
Linked notes
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