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

HRID 612762Notes

Reaction equation

HRID 612762 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

Reactant 3

HCID 176Acetic AcidHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 86584012Ethyl orthocarbonate

Product 1

HCID 15434963Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-2-ethoxy-1H-benzimidazole-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 (1.0 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.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate 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
  5. customto give crystals
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ecdc40fa830d4a0aa7e157e2c300410c
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

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