Potassium Carbonate → N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233063

Reaktionsgleichung

Reaktionsgleichung von HRID 233063
[C:1]([O:4][CH:5]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([NH2:17])[C:13]([I:18])=[C:12]([C:19]([NH:21][CH2:22][CH:23]([O:29][C:30](=[O:32])[CH3:31])[CH2:24][O:25][C:26](=[O:28])[CH3:27])=[O:20])[C:11]=1[I:33])=[O:9])(=[O:3])[CH3:2].[Br:39][CH:40]([CH2:44][CH2:45]Br)[C:41](Br)=[O:42].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[C:1]([O:4][CH:5]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:45][CH2:44][CH:40]([Br:39])[C:41]2=[O:42])[C:13]([I:18])=[C:12]([C:19]([NH:21][CH2:22][CH:23]([O:29][C:30](=[O:32])[CH3:31])[CH2:24][O:25][C:26](=[O:28])[CH3:27])=[O:20])[C:11]=1[I:33])=[O:9])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide TetraacetateHCID 112898262,4-dibromobutanoyl Bromide

Produkt 1

HCID 19048424N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]2,4,6-triiodo-1,3-benzenedicarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of N,N'-bis-[2,3-diacetyloxypropyl]-5-amino-2,4,6-triiodo-1,3-benzenedicar boxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (100 ml) was treated with 2,4-dibromobutyroyl bromide (4.02 g, 13.0 mmol) under an atmosphere of nitrogen and the reaction mixture was stirred for 50 hours at ambient temperature. The mixture was then treated with ground potassium carbonate (1.65 g, 12.0 mmol) and stirred for 30 minutes at ambient temperature. An additional portion (1.65 g, 12.0 mmol) of finely ground potassium carbonate was added and the mixture was stirred for 1.9 hours. The suspended salts were filtered and the solvent was evaporated to obtain a brown oil. This crude product was purified by silica gel flash chromatography to isolate N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]2,4,6-triiodo-1,3-benzenedicarboxamide, as a white powder (7.28 g, 71% yield), m.p. 110°-112°.

Aufarbeitung

  1. stirringstirred for 30 minutes at ambient temperature
  2. stirringthe mixture was stirred for 1.9 hours
  3. filtrationThe suspended salts were filtered
  4. customthe solvent was evaporated
  5. customto obtain a brown oil
  6. customThis crude product was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bb8e395e9c6b4812b5103d40111acd54
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591846

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