Glycidol → Iohexol

HRID 1457417

Reaktionsgleichung

Reaktionsgleichung von HRID 1457417
[NH:1]([C:5]1[C:6]([I:29])=[C:7]([C:21]([NH:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])=[O:22])[C:8]([I:20])=[C:9]([C:12]([NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])=[O:13])[C:10]=1[I:11])[C:2]([CH3:4])=[O:3].C[O-].[Na+].[CH2:33]1[O:35][CH:34]1[CH2:36][OH:37]>CO.COCCO>[CH3:4][C:2]([N:1]([C:5]1[C:10]([I:11])=[C:9]([C:12]([NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])=[O:13])[C:8]([I:20])=[C:7]([C:21]([NH:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])=[O:22])[C:6]=1[I:29])[CH2:33][CH:34]([OH:35])[CH2:36][OH:37])=[O:3]

Komponenten

6

Edukt 3

HCID 11164GlycidolHCID 10942334Sodium MethoxideHCID 111153265-Acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide2×

Produkt 1

HCID 3730IohexolAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5.0 gram 5-acetamino-N,N'-bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzene-dicarboxamide (Compound 1), 0.36 gram of 25% sodium methoxide in methanol, and 1.5 gram glycidol are combined in 2-methoxyethanol and heated to 90° C. for four hours. Solvent is removed under vacuum followed by dissolution of the residue in water. The solution is treated with 1 gram each of Amberlyst A-15 and Amberlite IRA-67 ion-exchange resins to remove sodium methoxide. Water is removed under vacuum to afford an oil. Crystallization from methanol/isopropanol (10:75) afforded 3.5 gram (64.6%) iohexol.

Aufarbeitung

  1. customSolvent is removed under vacuum
  2. dissolutionfollowed by dissolution of the residue in water
  3. additionThe solution is treated with 1 gram each of Amberlyst A-15 and Amberlite IRA-67 ion-exchange resins
  4. customto remove sodium methoxide
  5. customWater is removed under vacuum
  6. customto afford an oil
  7. customCrystallization from methanol/isopropanol (10:75)

Quellen und Nachweise

ORD-Eintrag
ord-04ece25d1e684e0ca9e702346e883205
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05847212

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