Metronidazole → HCID 70169093, compound

HRID 2230074Notes

Reaction equation

HRID 2230074 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](O)=[O:17])=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.S(Cl)(Cl)=O.[CH3:23][C:24]1[N:28]([CH2:29][CH2:30][OH:31])[C:27]([N+:32]([O-:34])=[O:33])=[CH:26][N:25]=1>>[CH3:23][C:24]1[NH:28][C:27]([N+:32]([O-:34])=[O:33])=[CH:26][N:25]=1.[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([O:31][CH2:30][CH3:29])=[O:17])=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

4

Reactant 3

HCID 4173MetronidazoleHCID 24386Thionyl ChlorideHCID 105871659-oxo-9H-thioxanthene-3-carboxylic acid

Product 1

HCID 70169093HCID 70169093, compoundYield 52.4%

Procedure

The reaction mixture of 9-oxo-9H-thioxanthene-3-carboxylic acid (288 mg, 1.0 mmol) and thionyl chloride (2 ml) was refluxed for 2 h. The excessive thionyl chloride was evaporated under the vacuum. The residue was dissolved in 3 ml of pyridine. To this solution, metronidazole (125 mg, 0.70 mmol) was added. After the mixture was stirred at room temperature for 4 h, then pyridine was removed in vacuo. The residue was dissolved in dichloromethane (50 ml). 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-CHCI3 to give 151 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl 9-oxo-9H-thioxanthene-3-carboxylate. m.p.: 128-130° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excessive thionyl chloride was evaporated under the vacuum
  3. dissolutionThe residue was dissolved in 3 ml of pyridine
  4. custompyridine was removed in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  6. washThe organic layer of dichloromethane was washed with 5% Na2CO3, H2O, and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed
  9. customthe residue was recrystallized from C2H5OH-CHCI3

Sources & evidence

ORD record
ord-85efd9c77901430db2aa73c8bd3cecda
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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