5-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide Tetraacetate → N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233069

Reaktionsgleichung

Reaktionsgleichung von HRID 233069
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][Br:9])[C:3](Br)=[O:4].[C:10]([O:13][CH:14]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[CH2:15][NH:16][C:17]([C:19]1[C:24]([I:25])=[C:23]([NH2:26])[C:22]([I:27])=[C:21]([C:28]([NH:30][CH2:31][CH:32]([O:38][C:39](=[O:41])[CH3:40])[CH2:33][O:34][C:35](=[O:37])[CH3:36])=[O:29])[C:20]=1[I:42])=[O:18])(=[O:12])[CH3:11]>CN(C)C(=O)C>[C:10]([O:13][CH:14]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[CH2:15][NH:16][C:17]([C:19]1[C:24]([I:25])=[C:23]([NH:26][C:3](=[O:4])[CH:2]([Br:1])[CH2:6][CH2:7][CH2:8][Br:9])[C:22]([I:27])=[C:21]([C:28]([NH:30][CH2:31][CH:32]([O:38][C:39](=[O:41])[CH3:40])[CH2:33][O:34][C:35](=[O:37])[CH3:36])=[O:29])[C:20]=1[I:42])=[O:18])(=[O:12])[CH3:11]

Komponenten

4

Edukt 2

HCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide TetraacetateHCID 111630822,5-dibromopentanoyl Bromide

Produkt 1

HCID 19048400N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

2,5-Dibromopentanoyl bromide (11 g, 34 mmol ) was added dropwise to a stirred solution of N,N'-bis[2,3bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (23.0 g, 26.3 mmol) in N,N-dimethylacetamide (240 ml) at 0°. After the addition, the reaction mixture was stirred at 0° for 1 hour, and then at room temperature for 20 hours. The solvent was removed in vacuo at 45° and the resulting solid was dissolved in ethyl acetate (400 ml). The organic layer was washed with saturated aqueous sodium bicarbonate (1×70 ml), water (1×70 ml) and saturated sodium chloride (1×70 ml). After drying over magnesium sulfate, the solvent was removed in vacuo to obtain a yellow residue (28 g). Purification by column chromatography over silica gel furnished pure N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide as an off-white crystalline compound (20.2 g, yield 69%).

Aufarbeitung

  1. additionAfter the addition
  2. waitat room temperature for 20 hours
  3. customThe solvent was removed in vacuo at 45°
  4. dissolutionthe resulting solid was dissolved in ethyl acetate (400 ml)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate (1×70 ml), water (1×70 ml) and saturated sodium chloride (1×70 ml)
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-691da5883b354f46a8b9541cb04d10a7
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591846

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