Hydrochloric Acid → 5-[Imino[(methoxycarbonyl)amino]methyl]-2-benzofurancarboxylic acid

HRID 1682668Notes

Reaction equation

HRID 1682668 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][C:9]=2[CH:18]=1)(=[NH:4])[NH2:3].[C:19](Cl)(=[O:22])[O:20][CH3:21].[OH-].[Na+].Cl>O.O1CCCC1.C(Cl)Cl>[CH3:21][O:20][C:19]([NH:3][C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][C:9]=2[CH:18]=1)=[NH:4])=[O:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide2×HCID 18919516HCID 18919516, compound

Product 1

HCID 1403812405-[Imino[(methoxycarbonyl)amino]methyl]-2-benzofurancarboxylic acidYield 187.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methylene chloride (2 ml) was added to ethyl 5-amidino-2-benzofurancarboxylate hydrochloride (100 mg, 0.372 mmol), and methyl chlorocarbonate (30 μl, 0.391 mmol) and then, a 0.2N aqueous sodium hydroxide solution (0.391 ml, 0.782 mmol) was added at room temperature, which was followed by vigorous stirring for 10 minutes. Methylene chloride (15 ml) was added to the reaction mixture. The mixture was washed with water and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure to give 88.0 mg of ethyl 5-(methoxycarbonylamidino)-2-benzofurancarboxylic as a colorless solid (82%). Tetrahydrofuran (2 ml), water (2 ml) and a 1N aqueous sodium hydroxide solution (2 ml, 2 mmol) were added to the compound (73.0 mg, 0.252 mmol), and the mixture was stirred at room temperature for one hour. 1N Hydrochloric acid was added to the reaction mixture to adjust its pH to 2-3, and low boiling matters were distilled away under reduced pressure to give 183 mg of 5-(methoxycarbonylamidino)-2-benzofurancarboxylic acid as a yellow solid (inclusive of sodium chloride).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationAfter filtration, low boiling matters
  4. distillationwere distilled away from the filtrate under reduced pressure
  5. customto give 88.0 mg of ethyl 5-(methoxycarbonylamidino)-2-benzofurancarboxylic as a colorless solid (82%)
  6. stirringthe mixture was stirred at room temperature for one hour
  7. distillationwere distilled away under reduced pressure

Sources & evidence

ORD record
ord-f157caa2c7b94b73b4ebd11789c6e3d4
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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