3,4-Diaminophenol → HCID 178471172, compound

HRID 412720Notes

Reaction equation

HRID 412720 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[NH2:8].C(ON[C:14]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=N)C>C(O)C>[OH:9][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:14]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:1][C:2]=2[CH:3]=1

Participants

4

Reactant 2

HCID 27729703,4-DiaminophenolHCID 178475099HCID 178475099, compound

Product 1

HCID 178471172HCID 178471172, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising of 3,4-diaminophenol (3.661 g, 29.5 mL), ethyl 2-(N-ethoxyamidino)propionate (7.423 g, 38.4 mmol) and ethanol (30 mL) was heated at reflux for 6 hours and concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL) and the solution was washed with saturated aqueous sodium hydrogencarbonate (3×20 mL) and brine (1×20 mL), dried (MgSO4) and concentrated in vacuo to provide ethyl 2-(5-hydroxy-1H-benzoimidazol-2-yl)propionate (6.3 g, 91% yield) as a dark solid. The solid was further purified by silica gel flash chromatography (100% ethyl acetate); MS (PB-PCI) C12H14N2O3 m/e calc 234.28; found 235 (MH+).

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  4. washthe solution was washed with saturated aqueous sodium hydrogencarbonate (3×20 mL) and brine (1×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae156290432a43d1bd88cde356c25497
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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