Hydrochloric Acid → 5-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide Tetraacetate

HRID 618927Notes

Reaction equation

HRID 618927 reaction equation
[NH2:1][C:2]1[C:3]([I:26])=[C:4]([C:18]([NH:20][CH2:21][CH:22]([OH:25])[CH2:23][OH:24])=[O:19])[C:5]([I:17])=[C:6]([C:15]=1[I:16])[C:7]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])=[O:8].C(O[C:31](=[O:33])[CH3:32])(=O)C.C([O:37][CH2:38][CH3:39])(=O)C.Cl>N1C=CC=CC=1>[NH2:1][C:2]1[C:15]([I:16])=[C:6]([C:7]([NH:9][CH2:10][CH:11]([O:14][C:31](=[O:33])[CH3:32])[CH2:12][O:13][C:38](=[O:37])[CH3:39])=[O:8])[C:5]([I:17])=[C:4]([C:3]=1[I:26])[C:18]([NH:20][CH2:21][CH:22]([O:25][C:12](=[O:13])[CH3:11])[CH2:23][O:24][C:7](=[O:8])[CH3:6])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 103950115-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

Product 1

HCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide Tetraacetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)isophthalamide (14.08 g, 0.02 mol), which had been prepared according to GB-A-1548594 was suspended in pyridine (200 ml) and acetic anhydride (57.1 g, 0.56 mol) was added dropwise with stirring and cooling. After stirring overnight, the mixture was poured into ethyl acetate (300 ml) and 20% aqueous HCl (200 ml). After extraction, the organic phase was washed with 2M aqueous HCl (20 ml), brine (70 ml), dried (Na2SO4) and evaporated. Yield 17.4 g (100%). The crude material was used without further purification, since analysis by HPLC and 1H NMR indicated, that the product was >97% pure.

Workup

  1. temperaturecooling
  2. stirringAfter stirring overnight
  3. extractionAfter extraction
  4. washthe organic phase was washed with 2M aqueous HCl (20 ml), brine (70 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was used without further purification, since analysis by HPLC and 1H NMR

Sources & evidence

ORD record
ord-413101b94a4c4bb3b879d708616d9ac4
Source dataset
uspto-grants-1999_09
Patent number
US05958375

Reaction notes

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