Acetic Acid → Methyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-2-ethoxy-1H-benzimidazole-7-carboxylate
Reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:16][CH:15]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(O)(=O)C.[C:32]([O-])([O-])([O-])[O:33][CH2:34][CH3:35]>>[C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:12]2[C:3]3[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=3[N:1]=[C:32]2[O:33][CH2:34][CH3:35])=[CH:15][CH:16]=1)#[N:27]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (2.03 g) in ethyl orthocarbonate (5 ml) was added acetic acid (0.37 g), and the mixture was stirred for one hour at 80° C. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogencarbonate and water. The solvent was evaporated to dryness to give crystals. Recrystallization of the crystals from ethyl acetate-hexane afforded colorless crystals (2.01 g, 86%). m.p.168.5°-169.5° C.
Workup
- concentrationThe reaction mixture was concentrated
- dissolutionthe residue was dissolved in ethyl acetate
- washThe solution was washed with an aqueous solution of sodium hydrogencarbonate and water
- customThe solvent was evaporated to dryness
- customto give crystals
- customRecrystallization of the crystals from ethyl acetate-hexane afforded colorless crystals (2.01 g, 86%)
Sources & evidence
- ORD record
- ord-77954638ef614ceb8d38643bf0d6e62c
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05736555
Reaction notes
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