Methanol → HCID 69131888, compound

HRID 349484Notes

Reaction equation

HRID 349484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[C:13]([OH:20])=[CH:14][CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:26]O>>[CH3:26][O:18][C:17]([C:16]1[C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[NH:12][C:11]=2[C:13]([OH:20])=[CH:14][CH:15]=1)=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69131253HCID 69131253, compound

Product 1

HCID 69131888HCID 69131888, compoundYield 76%

Procedure

2-(4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid (500 mg, 1.84 mmol) obtained in step 3 was dissolved in methanol, H2SO4 (0.49 ml, 9.20 mmol) was added dropwise thereto and refluxed for 15 hours. The resulting solution was cooled to room temperature, concentrated under a reduced pressure to remove methanol, and the residue was neutralized with NaHCO3. Then, the neutralized residue was extracted with ethyl acetate and concentrated under a reduced pressure to obtain a residue which was purified by silica gel chromatography to obtain the title compound (397 mg, 1.39 mmol) in a yield of 76%.

Workup

  1. temperaturerefluxed for 15 hours
  2. concentrationconcentrated under a reduced pressure
  3. customto remove methanol
  4. extractionThen, the neutralized residue was extracted with ethyl acetate
  5. concentrationconcentrated under a reduced pressure
  6. customto obtain a residue which
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3c4c9a6f9b85460b8a347d8c6945a829
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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