Methanol → HCID 69131504, compound

HRID 349474Notes

Reaction equation

HRID 349474 reaction equation
[Cl: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]([Cl: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 69119151HCID 69119151, compound

Product 1

HCID 69131504HCID 69131504, compoundYield 80%

Procedure

2-(4-chloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid (200 mg, 0.69 mmol) obtained in step 3 was dissolved in 5 ml of methanol, H2SO4 (0.18 ml, 3.45 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 1M 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 column chromatography (eluent—MeOH/CDCl3=5/95, Merck, Silicagel 60) to obtain the title compound (166 mg, 0.55 mmol) in a yield of 80%.

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 column chromatography (eluent—MeOH/CDCl3=5/95, Merck, Silicagel 60)

Sources & evidence

ORD record
ord-45ae475c6a8b4aac866e349694a6884b
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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