Acetic Acid → Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-2-ethoxy-1H-benzimidazole-7-carboxylate
Reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:21][CH:20]=2)=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:33]([O-])([O-])([O-])[O:34][CH2:35][CH3:36]>>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]2[C:7]3[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=[CH:16][C:6]=3[N:5]=[C:33]2[O:34][CH2:35][CH3:36])=[CH:20][CH:21]=1)#[N:32]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
Acetic acid (0.2 g) was added to a solution of ethyl 3-amino-2[(2′-cyanobiphenyl-4-yl)methyl]aminobenzoate (1.0 g) in ethyl orthocarbonate (5 ml).. The mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated, and the concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and water. The solvent was evaporated to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (0.79 g, 69%), m.p. 131-132° C. Elemental Analysis for C26,H23N3O3:
Workup
- concentrationThe reaction mixture was concentrated
- dissolutionthe concentrate was dissolved in ethyl acetate
- washThe solution was washed with an aqueous solution of sodium hydrogen carbonate and water
- customThe solvent was evaporated
- customto give crystals
- customRecrystallization from ethyl acetate-benzene afforded colorless crystals (0.79 g, 69%), m.p. 131-132° C
Sources & evidence
- ORD record
- ord-7d59cae6b31b4314bb624fb2ae32926c
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06232334B1
Reaction notes
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