Hydrochloric Acid → HCID 18354914, compound

HRID 429663Notes

Reaction equation

HRID 429663 reaction equation
[CH:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:5]=2[N:4]=1)=[O:2].CC(=CC)C.P([O-])(O)(O)=[O:22].[Na+].Cl([O-])=O.[Na+].Cl>O.C(O)(C)(C)C>[C:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:5]=2[N:4]=1)([OH:22])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 18354851HCID 18354851, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 18354914HCID 18354914, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a suspension of methyl 2-formyl-1H-benzimidazole-4-carboxylate (460 mg) in a mixture of water (3.2 ml) and t-butyl alcohol (12 ml) were added 2-methyl-2-butene (700 mg) and sodium dihydrogenphosphate (387 mg) in water bath. To the mixture was added portionwise sodium chlorite (901 mg) and stirred for 1 day at same temperature. The reaction mixture was cooled in an ice bath, adjusted to pH 4 with 1N hydrochloric acid and the precipitate was collected by vacuum filtration. The precipitate was washed with ethyl acetate and methanol to give methyl 2-carboxy-1H-benzimidazole-4-carboxylate (400 mg).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washThe precipitate was washed with ethyl acetate and methanol

Sources & evidence

ORD record
ord-a1add6f8a71f422081b6abe63107e939
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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