Methanol → HCID 69131851, compound

HRID 349494Notes

Reaction equation

HRID 349494 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12]2[C:14]([OH:21])=[CH:15][CH:16]=[C:17]([C:18]([OH:20])=[O:19])[C:11]=2[N:10]=1.OS(O)(=O)=O.[CH3:27]O>>[CH3:27][O:19][C:18]([C:17]1[C:11]2[N:10]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Cl:1])[NH:13][C:12]=2[C:14]([OH:21])=[CH:15][CH:16]=1)=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 691323682-(2-chloro-4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 69131851HCID 69131851, compoundYield 67%

Procedure

2-(2-chloro-4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid (500 mg, 1.63 mmol) obtained in step 3 was dissolved in methanol, H2SO4 (0.43 ml, 8.15 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 (393 mg, 1.23 mmol) in a yield of 67%.

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-4061ddba0c22403d9186412e2f48b8ff
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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