Sodium Hydroxide → HCID 90229443, compound

HRID 1505777Notes

Reaction equation

HRID 1505777 reaction equation
[CH2:1]([O:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:6]=2[N:5]=1)[CH3:2].[N+:17]([O-])([O-:19])=[O:18].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:6]=2[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 15654707Methyl 2-ethoxy-1H-benzimidazole-4-carboxylate

Product 1

HCID 90229443HCID 90229443, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirring solution of methyl 2-ethoxy-1H-benzimidazole-4-carboxylate (prepared as described in J. Med. Chem., 1993, 36, 2182) (500 mg) in conc. sulfuric acid (5 mL), potassium nitrate (275 mg) was added portion-wise under ice-cooling, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was poured into ice, alkalified with aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the titled compound (595 mg) as white powder.

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was poured into ice
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e4facd13f00740b5a7a4c96ad8d4d390
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

Loading…