N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-2,4,6-triiodo-5-[3-(iodomethyl)-5-oxo-4-morpholinyl]-1,3-benzenedicarboxamide → N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[3-[(acetyloxy)methyl]-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 233067
[C:1]([O:4][CH2:5][CH:6]([NH:12][C:13]([C:15]1[C:20]([I:21])=[C:19]([N:22]2[C:27](=[O:28])[CH2:26][O:25][CH2:24][CH:23]2[CH2:29]I)[C:18]([I:31])=[C:17]([C:32]([NH:34][CH:35]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:36][O:37][C:38](=[O:40])[CH3:39])=[O:33])[C:16]=1[I:46])=[O:14])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]>C(O)(=O)C.C([O-])(=O)C.[Ag+]>[C:9]([O:8][CH2:7][CH:6]([NH:12][C:13]([C:15]1[C:20]([I:21])=[C:19]([N:22]2[C:27](=[O:28])[CH2:26][O:25][CH2:24][CH:23]2[CH2:29][O:4][C:1](=[O:3])[CH3:2])[C:18]([I:31])=[C:17]([C:32]([NH:34][CH:35]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH2:41][O:42][C:43](=[O:45])[CH3:44])=[O:33])[C:16]=1[I:46])=[O:14])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Komponenten

4

Edukt 1

HCID 10328806N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-2,4,6-triiodo-5-[3-(iodomethyl)-5-oxo-4-morpholinyl]-1,3-benzenedicarboxamide

Produkt 1

HCID 10486230N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[3-[(acetyloxy)methyl]-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11246Silver acetateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-2,4,6-triiodo-5-[3-(iodomethyl)-5-oxo-4-morpholinyl]-1,3-benzenedicarboxamide of example 7b (2.01 g, 1.83 mmol) in glacial acetic acid (35 ml), was added silver acetate (0.67 g, 4 mmol) and the mixture refluxed for 14 hours. The solvent was removed in vacuo at 40°, and the residue extracted with ethyl acetate (200 ml). The organic extract, after washing with saturated aqueous sodium bicarbonate (3×25 ml) and water (3×25 ml), was dried over anhydrous sodium sulfate. Removal of the solvent followed by purification of the crude product by column chromatography over silica gel, yielded analytically pure N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[3-[(acetyloxy)methyl]-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a white fluffy solid (1.5 g, 82% yield), m.p. 208°-210°.

Aufarbeitung

  1. temperaturethe mixture refluxed for 14 hours
  2. customThe solvent was removed in vacuo at 40°
  3. extractionthe residue extracted with ethyl acetate (200 ml)
  4. washThe organic extract, after washing with saturated aqueous sodium bicarbonate (3×25 ml) and water (3×25 ml)
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. customfollowed by purification of the crude product by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e9c26e8f494d4be9aea500d3cfaf55c3
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591846

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