Metronidazole → HCID 70170429, compound

HRID 2230076Notes

Reaction equation

HRID 2230076 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([C:16](O)=[O:17])[CH:12]=[CH:11][C:10]=2[C:9](=[O:19])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.S(Cl)(Cl)=O.[CH3:24][C:25]1[N:29]([CH2:30][CH2:31][OH:32])[C:28]([N+:33]([O-:35])=[O:34])=[CH:27][N:26]=1>O>[CH3:24][C:25]1[NH:29][C:28]([N+:33]([O-:35])=[O:34])=[CH:27][N:26]=1.[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([C:16]([O:32][CH2:31][CH3:30])=[O:17])[CH:12]=[CH:11][C:10]=2[C:9](=[O:19])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 4173MetronidazoleHCID 24386Thionyl ChlorideHCID 670302-Anthraquinonecarboxylic acid

Product 1

HCID 70170429HCID 70170429, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The reaction mixture of 9,1 0-dihydro-9,10-dioxo-2-anthracenecarboxylic acid (126 mg, 0.5 mmol) and thionyl chloride (2 ml) was refluxed for 2 h. The excessive thionyl chloride was evaporated under vacuum. The residue was dissolved in 5 ml of pyridine. To this solution, metronidazole (80 mg, 0.47 mmol) was added. After the mixture was stirred at 80° C. for 2 h, water was added to this mixture. The water layer was extracted with dichloromethane (20 ml×3). The organic layer of dichloromethane was washed with 5% Na2CO3, H2O, and brine, and then dried over MgSO4. The solvent was removed, and the residue was recrystallized from C2H5OH—EtOAc to give 17 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl 9,10-dihydro-9,10-dioxo-2-anthracenecarboxylate. m.p.: 223-225 ° (dec.).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excessive thionyl chloride was evaporated under vacuum
  3. dissolutionThe residue was dissolved in 5 ml of pyridine
  4. extractionThe water layer was extracted with dichloromethane (20 ml×3)
  5. washThe organic layer of dichloromethane was washed with 5% Na2CO3, H2O, and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed
  8. customthe residue was recrystallized from C2H5OH—EtOAc

Sources & evidence

ORD record
ord-252ca5db989a47eeb3a82248e207b608
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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