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

HRID 5037Notes

Reaction equation

HRID 5037 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.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]2[N:29]=[CH:30][NH:31][C:27]=2[CH:26]=1>>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]2[N:29]([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:30]=[N:31][C:27]=2[CH:26]=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]2[N:29]=[CH:30][N:31]([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:27]=2[CH:26]=1

Participants

4

Reactant 2

HCID 785985-methoxy-1H-benzimidazoleHCID 10448388Methyl (E)-11-(2-chloroethylidene)-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Product 2

HCID 10410194methyl (E)-11-[2-(5-methoxy-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylateHCID 10477545methyl (E)-11-[2-(6-methoxy-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Procedure

Compound h, 2.9 g, and 4.2 g of 5-methoxybenzimidazole were treated in a manner similar to Example 23 to give a 1:1 mixture of Compounds E-61a and E-62a. The mixture was separated and purified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1) to give 0.8 g of methyl (E)-11-[2-(5-methoxy-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound E-61a), 0.5 g of methyl (E)-11-[2-(6-methoxy-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound E-62a) and 2.3g of the mixture of Compounds E-61a and E-62a.

Workup

  1. customto give
  2. additiona 1:1 mixture of Compounds E-61a and E-62a
  3. customThe mixture was separated
  4. custompurified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1)

Sources & evidence

ORD record
ord-598fc3b6cb7148718b860b1c0cc3f13a
Source dataset
uspto-grants-1993_09
Patent number
US05242931

Reaction notes

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