Tetrahydrofuran → HCID 86758373, compound

HRID 2230066Notes

Reaction equation

HRID 2230066 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].O[CH2:13][CH2:14][CH2:15][N:16]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][N:18]=[C:17]1[CH3:24].CCN=C=NCCCN(C)C.C1COCC1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:24][C:17]1[NH:16][C:20]([N+:21]([O-:23])=[O:22])=[CH:19][N:18]=1.[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68944Ternidazole

Product 1

HCID 86758373HCID 86758373, compound

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), 1-(3-hydroxypropyl)-2-methyl-5-nitroimidazole (184 mg, 1.0 mmol), EDCI (260 mg, 1.3 mmol), DMAP (10 mg, 0.1 mmol) and THF (5 ml) will be stirred at room temperature for 10 h. Evaporation of THF gives a residue which will be dissolved in ethyl acetate. The organic layer of ethyl acetate will be washed with H2O, 5% Na2CO3, H2O and brine, and then dried over MgSO4. The solvent will be removed under vacuum. The resulting solid will be recrystallized from C2H5OH to give 2-methyl-5-nitro-1H-imidazole-1-propyl 5-nitro-2-furoate.

Workup

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

Sources & evidence

ORD record
ord-6818a41e648c4729852d93a1dba42897
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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