Sodium Hydroxide → HCID 59615355, compound

HRID 1505757Notes

Reaction equation

HRID 1505757 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[N:3]=[CH:2]1.[N+:14]([O-])([O-:16])=[O:15].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[N+:14]([C:7]1[CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]2[N:3]=[CH:2][NH:1][C:5]=2[CH:6]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 14970852Methyl 1H-benzimidazole-4-carboxylate

Product 1

HCID 59615355HCID 59615355, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Methyl 1H-benzimidazole-4-carboxylate (315 mg) was dissolved in conc. sulfuric acid (3 mL), and the solution was stirred on ice bath. A small amount of potassium nitrate (199 mg) was added portion-wise, and the solution was stirred at room temperature for 4 hours. The reaction mixture was poured into ice, alkalified with 3N aqueous sodium hydroxide solution under stirring on ice bath, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, and dried over anhydrous magnesium sulfate. The titled compound (334 mg) was obtained as colorless powder after distilling off the solvent under reduced pressure.

Workup

  1. stirringthe solution was stirred at room temperature for 4 hours
  2. additionThe reaction mixture was poured into ice
  3. stirringunder stirring on ice bath
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-9616e3132db94e40bb011758e41433f1
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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