Hydrochloric Acid → HCID 178524169, compound

HRID 1945476Notes

Reaction equation

HRID 1945476 reaction equation
C[O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]2[NH:9][C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].Cl.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]2[NH:9][C:8]3[CH:23]=[CH:24][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178497369HCID 178497369, compound

Product 1

HCID 178524169HCID 178524169, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 2-(4-nitro-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (90 mg, 0.27 mmol), acetic acid (15 mL) and coned HCl (20 mL) was heated under reflux for 3 h. At the end of the reaction period, the mixture was cooled to 10° C., neutralize with aqueous sodium bicarbonate solution, filtered, washed with ethyl acetate (10 mL), water (50 mL) and dried to afford 2-(4-nitro-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid as a colorless powder (0.078 g, 90% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customAt the end of the reaction period
  4. filtrationfiltered
  5. washwashed with ethyl acetate (10 mL), water (50 mL)
  6. customdried

Sources & evidence

ORD record
ord-85016f86082e4eb0a9f1915ae54e6cbe
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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