Acetic Acid → Methyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate

HRID 612764Notes

Reaction equation

HRID 612764 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]#[N:31])=[CH:20][CH:19]=2)=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].[C:32]([O-])([O-])([O-])[O:33][CH2:34][CH3:35]>>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:16]2[C:7]3[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=[CH:15][C:6]=3[N:5]=[C:32]2[O:33][CH2:34][CH3:35])=[CH:19][CH:20]=1)#[N:31]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 15654653Methyl 3-amino-2-{[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino}benzoateHCID 86584012Ethyl orthocarbonate

Product 1

HCID 15654674Methyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate

Conditions

Temperature
80 °C

Procedure

Acetic acid (0.37 g) was added to a solution of methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (2.03 g) in ethyl orthocarbonate (5 ml), and the mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated to dryness and the residue was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and water. The solvent was evaporated in vacuo to give crystals. Recrystallization from ethyl acetate--hexane afforded colorless crystals (2.01 g, 86%), m.p. 168.5-169.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  4. customThe solvent was evaporated in vacuo
  5. customto give crystals
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b9cfb3cae1c243648dc3cd9f43196edc
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

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