Tetraethylammonium acetate → 2,4,6-Triiodoisophthalamide

HRID 977808

Reaktionsgleichung

Reaktionsgleichung von HRID 977808
ICC1CCC(=O)N1[C:9]1[C:10]([I:23])=[C:11]([C:20]([NH2:22])=[O:21])[C:12]([I:19])=[C:13]([C:16]([NH2:18])=[O:17])[C:14]=1[I:15].C([O-])(=O)C.C([N+](CC)(CC)CC)C>C(#N)C>[I:19][C:12]1[C:13]([C:16]([NH2:18])=[O:17])=[C:14]([I:15])[CH:9]=[C:10]([I:23])[C:11]=1[C:20]([NH2:22])=[O:21]

Komponenten

4

Edukt 2

HCID 102017Tetraethylammonium acetateHCID 867506195-[2-(Iodomethyl)-5-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Produkt 1

HCID 221238242,4,6-TriiodoisophthalamideAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of N,N'-bis[2-(acetyloxy)-1-(acetyloxy)methyl]ethyl]-5-[2-(iodomethyl)-5-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (12.00 g, 110 mmol) in acetonitrile (150 ml) was added tetraethylammonium acetate (5.74 g, 22 mmol) and the mixture stirred at 50° for 18 hours. Acetonitrile was removed in vacuo at 60°, the residue dissolved in ethyl acetate (200 ml), and the resulting solution washed with brine (2×100 ml) and with water (100 ml). The ethyl acetate layer was dried and removal of the solvent afforded the crude product as a colorless glassy solid. This material was purified by column chromatography over silica gel, using 20% hexane in ethyl acetate as eluent, to obtain N, N-bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[2-(acetyloxy)methyl)-5-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a colorless solid (9.4 g, 83.6% yield).

Aufarbeitung

  1. customAcetonitrile was removed in vacuo at 60°
  2. dissolutionthe residue dissolved in ethyl acetate (200 ml)
  3. washthe resulting solution washed with brine (2×100 ml) and with water (100 ml)
  4. dry with materialThe ethyl acetate layer was dried
  5. customremoval of the solvent
  6. customafforded the crude product as a colorless glassy solid
  7. customThis material was purified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1726a8b8a348401bb2464f509803b50a
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614638

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