5-Chlorovaleryl chloride → N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(5-chloro-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 1779871Notes

Reaction equation

HRID 1779871 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[C:9]([O:12][CH:13]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:14][NH:15][C:16]([C:18]1[C:23]([I:24])=[C:22]([NH2:25])[C:21]([I:26])=[C:20]([C:27]([NH:29][CH2:30][CH:31]([O:37][C:38](=[O:40])[CH3:39])[CH2:32][O:33][C:34](=[O:36])[CH3:35])=[O:28])[C:19]=1[I:41])=[O:17])(=[O:11])[CH3:10]>>[C:9]([O:12][CH:13]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:14][NH:15][C:16]([C:18]1[C:23]([I:24])=[C:22]([NH:25][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[C:21]([I:26])=[C:20]([C:27]([NH:29][CH2:30][CH:31]([O:37][C:38](=[O:40])[CH3:39])[CH2:32][O:33][C:34](=[O:36])[CH3:35])=[O:28])[C:19]=1[I:41])=[O:17])(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 740895-Chlorovaleryl chlorideHCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide Tetraacetate

Product 1

HCID 19048404N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(5-chloro-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamideYield 97%

Procedure

5-Chloropentanoyl chloride (5.1 g, 33 mmol) was added dropwise to a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (20.5 g, 23 mmol) in N,N'-dimethylacetamide (75 ml) at 0°-5°. The reaction mixture was stirred at 5° for 1 hour, and then at room temperature for 30 hours. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (250 ml). The solution was washed with water (2×50 ml), followed by saturated aqueous NaCl (50 ml), and then dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(5-chloro-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide as an off-white fluffy solid (22.1 g, yield 97%, purity 98.5%).

Workup

  1. waitat room temperature for 30 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (250 ml)
  4. washThe solution was washed with water (2×50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-168eba845f2d40e1992d8fc898531413
Source dataset
uspto-grants-1997_05
Patent number
US05628980

Reaction notes

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