Hydrochloric Acid → 5-(2-Chloroacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

HRID 265752Notes

Reaction equation

HRID 265752 reaction equation
ClCC([O:5][CH:6]([CH2:41][O:42]C(=O)CCl)[CH2:7][NH:8][C:9](=[O:40])[C:10]1[C:31]([I:32])=[C:30]([NH:33][C:34](=[O:37])[CH2:35][Cl:36])[C:29]([I:38])=[C:12]([C:13]([NH:15][CH2:16][CH:17]([O:24]C(=O)CCl)[CH2:18][O:19]C(=O)CCl)=[O:14])[C:11]=1[I:39])=O.[OH-].[Na+].O.Cl>CN(C)C(=O)C.C(#N)C>[OH:5][CH:6]([CH2:41][OH:42])[CH2:7][NH:8][C:9](=[O:40])[C:10]1[C:31]([I:32])=[C:30]([NH:33][C:34](=[O:37])[CH2:35][Cl:36])[C:29]([I:38])=[C:12]([C:13]([NH:15][CH2:16][CH:17]([OH:24])[CH2:18][OH:19])=[O:14])[C:11]=1[I:39]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 110186155-(2-Chloroacetamido)-2,4,6-triiodo-N,N'-bis(2,3-bis(2-chloroacetoxy)propyl)isophthalamide

Product 1

HCID 111047205-(2-Chloroacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamideYield 92.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

N,N'-bis[2,3-di(2-chloroacetoxy)propyl]-5-(2-chloroacetamido)-2,4,6-triiodoisophthalamide in N,N-dimethylacetamide and acetonitrile, from Example 3, was hydrolyzed by adding 130 mL of 10N sodium hydroxide solution (1.3 moles). Water (36 mL) was then added to the mixture to give a homogeneous solution. 1N Hydrochloric acid (100 mL, 0.1 moles) was added to precipitate the N,N'-bis(2,3-dihydroxypropyl)-5-(2-chloroacetamido)-2,4,6-triiodoisophthalamide. The precipitate was collected and washed with water. The wet product was dried at 60° C. in a vacuum oven to give 71.6 g of product, 92.2% yield. The material was 100% pure by HPLC analysis.

Workup

  1. customto give a homogeneous solution
  2. customto precipitate the N,N'-bis(2,3-dihydroxypropyl)-5-(2-chloroacetamido)-2,4,6-triiodoisophthalamide
  3. customThe precipitate was collected
  4. washwashed with water
  5. customThe wet product was dried at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-8ec8a3e1b800432c82b1a269870a8aa1
Source dataset
uspto-grants-1997_07
Patent number
US05648536

Reaction notes

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