Metronidazole → HCID 86758374, compound

HRID 2230070Notes

Reaction equation

HRID 2230070 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13]1[N:17](CCO)[C:16]([N+:21]([O-:23])=[O:22])=[CH:15][N:14]=1.[CH3:24][CH2:25]N=C=NCCCN(C)C.C1COCC1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:12][C:13]1[NH:17][C:16]([N+:21]([O-:23])=[O:22])=[CH:15][N:14]=1.[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH2:24][CH3:25])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 4173MetronidazoleHCID 8028TetrahydrofuranHCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 86758374HCID 86758374, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The reaction mixture of 5-Nitro-2-furoic acid (157 mg, 1.0 mmol), metronidazole (161 mg, 0.94 mmol), EDCI (260 mg, 1.3 mmol), DMAP (10 mg, 0.1 mmol) and THF (5 ml) was stirred at room temperature for 10 h. Evaporation of THF gave a residue which was dissolved in ethyl acetate. The organic layer of ethyl acetate was washed with H2O, 5% Na2CO3, H2O and brine, and then dried over MgSO4. The solvent was removed under vacuum. The resulting solid was recrystallized from C2H5OH to give 134 mg (44.6%) 2-methyl-5-nitro-1H-imidazole-1-ethyl 5-nitro-2-furoate. m.p.: 150-152° C.

Workup

  1. customEvaporation of THF
  2. customgave a residue which
  3. washThe organic layer of ethyl acetate was washed with H2O, 5% Na2CO3, H2O and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under vacuum
  6. customThe resulting solid was recrystallized from C2H5OH

Sources & evidence

ORD record
ord-f0e3e24034ac4ab59d4286b7282cb11f
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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