Hydrochloric Acid → HCID 14856789, compound

HRID 1110809Notes

Reaction equation

HRID 1110809 reaction equation
Cl.[CH3:2][C:3]1[NH:4][C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.Cl.[CH3:16]O>>[CH3:2][C:3]1[NH:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:16])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 173682452-Methyl-1H-benzimidazole-5-carboxylic acid hydrochloride

Product 1

HCID 14856789HCID 14856789, compoundYield 93.2%

Procedure

Mass spectrum (FAB, Pos): m/z 177 (M+ +1, as a free base). ##STR15## 2-Methylbenzimidazole-5-carboxylic acid hydrochloride, 6.6 g (32.5 mmols), was added to 200 ml of methanol and 5 ml of conc. hydrochloric acid was added to the mixture followed by heating to reflux for 8 hours. The solvent was distilled off under reduced pressure and 200 ml of water was added to the residue. After 1 N sodium hydroxide solution was added to the mixture to adjust pH to 9 to 10, the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. The solvent was distilled off to give 5.5 g (93.2%) of methyl 2-methyl-benzimidazole-5-carboxylate.

Workup

  1. additionwas added to the mixture
  2. temperatureby heating
  3. temperatureto reflux for 8 hours
  4. distillationThe solvent was distilled off under reduced pressure and 200 ml of water
  5. additionwas added to the residue
  6. additionAfter 1 N sodium hydroxide solution was added to the mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9adf109a6694448bb2625f995fc465b7
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

Loading…