Metronidazole → HCID 86758375, compound

HRID 2230071Notes

Reaction equation

HRID 2230071 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:24][C:25]1[N:29](CCO)[C:28]([N+:33]([O-:35])=[O:34])=[CH:27][N:26]=1>>[CH3:24][C:25]1[NH:29][C:28]([N+:33]([O-:35])=[O:34])=[CH:27][N:26]=1.[CH2:24]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]([C:17]([O-:19])=[O:18])=[CH:16][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:25]

Participants

4

Reactant 3

HCID 4173MetronidazoleHCID 8593CinchophenHCID 24386Thionyl Chloride

Product 1

HCID 86758375HCID 86758375, compoundYield 16.1%

Conditions

Temperature
80 °C

Procedure

The reaction mixture of 2-Phenyl-4-quinolinecarboxylic acid (249 mg, 1.0 mmol) and thionyl chloride (1.5 ml) was refluxed for 2 h. The excessive thionyl chloride was evaporated undervacuum. The residue was dissolved in 5 ml of pyridine. To this solution, metronidazole (170 mg, 0.98 mmol) was added. The mixture solution was stirred at 80° C. for 2 h. Pyridine was removed under reduced pressure. The residue was dissolved in dichloromethane. The organic layer of CH2Cl2 was washed with saturated aqueous NaHCO3, H2O, and brine, and then dried over MgSO4. The solvent was removed under vacuum. The resulting yellow solid was recrystallized from CH3OH-EtOAc to give 32 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl2-phenyl-4-quinolinecarboxylate. m.p.: 122-124° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excessive thionyl chloride was evaporated undervacuum
  3. dissolutionThe residue was dissolved in 5 ml of pyridine
  4. customPyridine was removed under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washThe organic layer of CH2Cl2 was washed with saturated aqueous NaHCO3, H2O, and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed under vacuum
  9. customThe resulting yellow solid was recrystallized from CH3OH-EtOAc

Sources & evidence

ORD record
ord-c1ea3511214148cd8d5a524ddb4a8d8a
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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