Acetic Acid → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-methoxybenzimidazole-7-carboxylate

HRID 612761Notes

Reaction equation

HRID 612761 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

Reactant 3

HCID 176Acetic AcidHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 19872204Methyl orthocarbonate

Product 1

HCID 22596778Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-methoxybenzimidazole-7-carboxylate

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

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe concentrate was extracted with ethyl acetate
  3. washThe organic layer was then 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-c7fd13db7892440ba3ebe0e3516dee47
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

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