Iodine → 3,5-diethyl 4-iodo-1H-pyrazole-3,5-dicarboxylate

HRID 33274

Reaktionsgleichung

Reaktionsgleichung von HRID 33274
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[I:16]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:14]([O:13][C:11]([C:9]1[C:10]([I:16])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:7][N:8]=1)=[O:12])[CH3:15]

Komponenten

5

Edukt 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylate

Produkt 1

HCID 117392303,5-diethyl 4-iodo-1H-pyrazole-3,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 10 g 1H-Pyrazole-3,5-dicarboxylic acid diethyl ester in 400 ml acetonitrile 13 g ammonium cerium(iv) nitrate (CAN) and 7.17 g iodine were added and the mixture was heated to reflux for 5 h. Then, after cooling to RT, 30 ml sat. sodium thiosulfate solution were added. The mixture was extracted with ethyl acetate (3×100 ml), the combined organic layers were washed with water and then dried over MgSO4, filtered and the solvents were removed under reduced pressure. The residue was filtered through a pad of silica gel eluting with heptane/ethyl acetate 1:1.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 h
  3. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. filtrationThe residue was filtered through a pad of silica gel eluting with heptane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-0d5a393a7b0d42febfff4291922d7261
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429581B2

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