HCID 70057981, compound → HCID 10821636, compound

HRID 1110817Notes

Reaction equation

HRID 1110817 reaction equation
S(O)(O)(=O)=O.[CH3:6][N:7]1[C:11]2[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1>C(O)(=O)C.[C].[Pd]>[CH3:6][N:7]1[C:11]2[CH2:12][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:15][C:10]=2[N:9]=[CH:8]1

Participants

4

Reactant 1

HCID 70057981HCID 70057981, compound

Product 1

HCID 10821636HCID 10821636, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3.39 g of methyl 1-methylbenzimidazole-6-carboxylate sulfate in 70 ml of acetic acid was catalytically hydrogenated at 90° C. for 6 hours under 60 atms using 1.9 g of 5% palladium carbon as a catalyst. Ater the catalyst was filtered off and the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the concentrate followed by extraction with 0.5 N HCl. The aqueous phase was rendered alkaline with potassium carbonate and extracted with chloroform. The chloroform phase was washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2.10 g (92%) of methyl 1-methyl-4,5,6,7-tetrahydrobenzimidazole-6-carboxylate.

Workup

  1. filtrationAter the catalyst was filtered off
  2. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the concentrate
  4. extractionfollowed by extraction with 0.5 N HCl
  5. extractionextracted with chloroform
  6. washThe chloroform phase was washed with saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-016982e6a9bc4fe198039eea1322fbb4
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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