Sodium Hydroxide → 6-[[2-Ethoxy-1-phenyl-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

HRID 460533Notes

Reaction equation

HRID 460533 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1.[CH2:25]([O:27][C:28](OCC)(OCC)OCC)[CH3:26].[OH-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]2[N:16]=[C:28]([O:27][CH2:25][CH3:26])[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66213Tetraethyl orthocarbonateHCID 120430856-(3-Phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester

Product 1

HCID 102214996-[[2-Ethoxy-1-phenyl-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

200 mg of 6-(3-phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester was mixed with 0.19 ml of tetraethylorthocarbonate and 40 μl of acetic acid, and the mixture was heated for 4 hours to 80° C. After cooling, it was mixed with 1N sodium hydroxide solution, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 124 mg was obtained.

Workup

  1. temperaturethe mixture was heated for 4 hours to 80° C
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue was purified by column chromatography on silica gel
  8. custom124 mg was obtained

Sources & evidence

ORD record
ord-171167bcfd7441389006929094d04ae9
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Reaction notes

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