Acetic Acid → Ioversol

HRID 265750Notes

Reaction equation

HRID 265750 reaction equation
C(OCCCC(O[N:11]([C:15]1[C:16]([I:51])=[C:17]([C:37]([NH:39][CH2:40][CH:41]([O:47]C(=O)C)[CH2:42][O:43]C(=O)C)=[O:38])[C:18]([I:36])=[C:19]([C:34]=1[I:35])[C:20]([NH:22][CH2:23][CH:24]([O:30]C(=O)C)[CH2:25][O:26]C(=O)C)=[O:21])[C:12](=[O:14])[CH3:13])=O)(=O)C.S(=O)(=O)(O)[OH:53].[C:57](O)(=O)[CH3:58].[OH2:61]>>[CH2:57]([N:11]([C:12]([CH2:13][OH:53])=[O:14])[C:15]1[C:16]([I:51])=[C:17]([C:37]([NH:39][CH2:40][CH:41]([OH:47])[CH2:42][OH:43])=[O:38])[C:18]([I:36])=[C:19]([C:20]([NH:22][CH2:23][CH:24]([OH:30])[CH2:25][OH:26])=[O:21])[C:34]=1[I:35])[CH2:58][OH:61]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 88081466HCID 88081466, compound

Product 1

HCID 3741Ioversol

Procedure

5-[N-(2-Acetoxyethyl)acetoxyacetamido]-N,N'bis(2,3-diacetoxypropy)-2,4,6-triiodoisophthalamide solids are slurried in hot water containing a catalytic quantity of sulfuric acid. The solid gradually dissolves as it is heated with the steam on the jacket. The material is hydrolyzed to produce crude ioversol and acetic acid as a by-product. To remove the acetic acid, clean steam is sparged into the reactor. The solution volume is maintained constant by adding deionized water during the reaction and acetic acid removal. The reaction is tested for completeness of hydrolysis and for the removal of acetic acid.

Workup

  1. dissolutionThe solid gradually dissolves as it
  2. temperatureis heated with the steam on the jacket

Sources & evidence

ORD record
ord-dbbb2a12a59841a8a346d453f7a7a35e
Source dataset
uspto-grants-1997_07
Patent number
US05648536

Reaction notes

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