Ethanol → Ethyl 1H-benzimidazole-6-carboxylate

HRID 2274717Notes

Reaction equation

HRID 2274717 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>>[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH2:18][CH3:19])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 4594565-Benzimidazolecarboxylic acid

Product 1

HCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

Procedure

Benzimidazole-5-carboxylic acid I (12.9 g, 0.08 mmol) was dissolved in 100 mL of EtOH and mL of conc. H2SO4 (0.088 mmol) were added. The solution was refluxed for 24 h. After that the mixture was poured on ice and brought to neutral pH. The resulting mixture was extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over Na2SO4. After that the solvent was removed under reduced pressure. Yield: 12.6 g, 83%

Workup

  1. temperatureThe solution was refluxed for 24 h
  2. additionAfter that the mixture was poured on ice
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×100 ml)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customAfter that the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-55d7e49e6dcc4d568f3c2af3b4a04a7b
Source dataset
uspto-grants-2015_09
Patent number
US09126987B2

Reaction notes

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