Reaktion #364667

Reaktionsgleichung

methyl 1-((2′-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate

trimethyltin azide

→

crystals

Ausbeute 56.8%

Methyl 2-ethoxy-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

Ausbeute 56.8%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwere heated
2. 2
   Temperaturunder reflux for one day
3. 3
   EinengenThe reaction mixture was concentrated to dryness
4. 4
   workup.ADDITIONTo the residue were added methanol (50 ml) and 1N-HCl (20 ml)
5. 5
   SonstigeAfter removal of the solvent
6. 6
   Sonstigethe residual syrup was purified by column chromatography on silica gel
7. 7
   Sonstigeto give crystals
8. 8
   SonstigeRecrystallization from ethyl acetate-benzene

Vorschrift

A mixture of methyl 1-((2′-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate (1.85 g) and trimethyltin azide (2.80 g) in toluene (15 ml) were heated under reflux for one day. The reaction mixture was concentrated to dryness. To the residue were added methanol (50 ml) and 1N-HCl (20 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was adjusted to about pH 3-4 with 1N-NaOH. After removal of the solvent, the residual syrup was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-benzene gave colorless crystals (1.16 g, 56%), m.p. 191-193° C. (decomp.).

Quelle