Phosphorus oxychloride → 6-[[2-chloro-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

HRID 460524

Reaction equation

HRID 460524 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:17][C:16](=O)[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]=2[CH:25]=1.P(Cl)(Cl)([Cl:29])=O.C(=O)(O)[O-].[Na+]>>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([Cl:29])[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]=2[CH:25]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 694331146-[[1-Phenyl-2-oxo-2,3-dihydro-1H-benzoimidazol-6-yl]oxy]hexanoic acid methyl ester

Product 1

HCID 694308016-[[2-chloro-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

Procedure

3 g of 6-[[1-phenyl-2-oxo-2,3-dihydro-1H-benzoimidazol-6-yl]oxy]hexanoic acid methyl ester was mixed with 12 ml of phosphorus oxychloride, and the mixture was refluxed for 4 hours. After cooling, it was stirred into saturated sodium bicarbonate solution, extracted three times with ethyl acetate, the combined organic phases were dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 1.28 g was obtained.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. customthe combined organic phases were dried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was purified by column chromatography on silica gel
  7. custom1.28 g was obtained

Sources & evidence

ORD record
ord-cfd90cf58cd541f1b6f269a84fb1ede5
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Linked notes

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