Methanol → HCID 69131835, compound

HRID 349470Notes

Reaction equation

HRID 349470 reaction equation
C[O:2][C:3]1[C:8]2[NH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[C:6]([C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1.OS(O)(=O)=O.[CH3:26]O>>[CH3:26][O:20][C:18]([C:6]1[C:7]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9][C:8]=2[C:3]([OH:2])=[CH:4][CH:5]=1)=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22663339HCID 22663339, compound

Product 1

HCID 69131835HCID 69131835, compoundYield 83%

Procedure

7-methoxy-2-phenyl-1H-benzoimidazole-4-carboxylic acid (2.00 g, 7.46 mmol) obtained in step 4 was dissolved in 30 ml of methanol, H2SO4 (2.00 ml, 37.28 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 purified by recrystallization from CHCl3/MeOH/hexane to obtain the title compound (1.7 g, 5.89 mmol) in a yield of 83%.

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. custompurified by recrystallization from CHCl3/MeOH/hexane

Sources & evidence

ORD record
ord-cca3992336ea4700989ec0ea29277d56
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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