Acetic Acid → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-methoxybenzimidazole-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][CH3:35]>>[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][CH3:35])=[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 (1.1 g) in methyl orthocarbonate (5 ml). The mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated, and the concentrate was extracted with ethyl acetate. The organic layer was then washed with an aqueous solution of sodium hydrogen carbonate and water. The solvent was evaporated in vacuo to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (1.09 g, 90%), m.p. 160-161° C.
Workup
- concentrationThe reaction mixture was concentrated
- extractionthe concentrate was extracted with ethyl acetate
- washThe organic layer was then washed with an aqueous solution of sodium hydrogen carbonate and water
- customThe solvent was evaporated in vacuo
- customto give crystals
- customRecrystallization from ethyl acetate-benzene afforded colorless crystals (1.09 g, 90%), m.p. 160-161° C.
Sources & evidence
- ORD record
- ord-5c2bdfd0289440b18e875b673b105f88
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06232334B1
Reaction notes
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