Water → HCID 178508281, compound

HRID 1844946Notes

Reaction equation

HRID 1844946 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:12]C(=O)C)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.OS(O)(=O)=O>CO>[C:1]1([C:7]2[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178474414HCID 178474414, compound

Product 1

HCID 178508281HCID 178508281, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the above 0.5 g (2.4 mmol) N-(4-phenyl-1H-imidazol-2-yl)-acetamide in MeOH (20 mL) was added water (20 mL) and conc. H2SO4 (1 mL). The mixture was refluxed under nitrogen for 2 days. After cooling to rt, the organic solvent was removed under vacuum. The reaction mixture was neutralized with saturated sodium bicarbonate aq. solution (50 mL) and extracted with ethyl acetate (150 mL). The organic layer was dried and condensed. The residue was purified by a flash column chromatography eluting with EtOAc then EtOAc/MeOH=7:1 to give 4-phenyl-1H-imidazol-2-ylamine (160 mg, 41%). LCMS: 160 (M+1)+.

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 2 days
  2. customthe organic solvent was removed under vacuum
  3. extractionextracted with ethyl acetate (150 mL)
  4. customThe organic layer was dried
  5. customcondensed
  6. customThe residue was purified by a flash column chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-655b48d31694443e8147dbb4ea442585
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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