4-Pentenoyl chloride → N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)-methyl]ethyl]-2,4,6-triiodo-5-[(1-oxo-4-pentenyl) amino]-1,3-benzenedicarboxamide

HRID 260540

Reaction equation

HRID 260540 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[C:8]([O:11][CH2:12][CH:13]([NH:19][C:20]([C:22]1[C:27]([I:28])=[C:26]([NH2:29])[C:25]([I:30])=[C:24]([C:31]([NH:33][CH:34]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[CH2:35][O:36][C:37](=[O:39])[CH3:38])=[O:32])[C:23]=1[I:45])=[O:21])[CH2:14][O:15][C:16](=[O:18])[CH3:17])(=[O:10])[CH3:9]>CC(N(C)C)=O>[C:37]([O:36][CH2:35][CH:34]([NH:33][C:31]([C:24]1[C:25]([I:30])=[C:26]([NH:29][C:1](=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5])[C:27]([I:28])=[C:22]([C:20]([NH:19][CH:13]([CH2:12][O:11][C:8](=[O:10])[CH3:9])[CH2:14][O:15][C:16](=[O:18])[CH3:17])=[O:21])[C:23]=1[I:45])=[O:32])[CH2:40][O:41][C:42](=[O:44])[CH3:43])(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 42284934-Pentenoyl chlorideHCID 11766168N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 10373691N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)-methyl]ethyl]-2,4,6-triiodo-5-[(1-oxo-4-pentenyl) amino]-1,3-benzenedicarboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Pentenoyl chloride (11.9 g, 100 mmol) was added to a stirred solution of N,N'-bis-[2-(acetyloxy)-1-[(acetyloxy)-methyl]ethyl]-5-amino-2,4,6 -triiodo-1,3-benzenedicarboxamide (47.75 g, 50 mmol) in dimethylacetamide (400 mL) at room temperature and the mixture was stirred for 16 hours. Dimethylacetamide was removed in vacuo and the residue dissolved in ethyl acetate (600 ml). The solution was washed with aqueous sodium bicarbonate (10%, 2×150 mL) and with water (2×100 mL) and brine (150 mL). The organic layer was dried and the solvent removed to obtain the crude product as an off-white solid. Further purification by crystallization from a mixture of acetone (250 mL) and hexane (75 mL) afforded the title A compound (42.5 g), m.p. 162°-64°. TLC: Rf 0.55 in ethyl acetate. Mass Spectrum: m/z 956 (M+H)+, 830, 653.

Workup

  1. customDimethylacetamide was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (600 ml)
  3. washThe solution was washed with aqueous sodium bicarbonate (10%, 2×150 mL) and with water (2×100 mL) and brine (150 mL)
  4. customThe organic layer was dried
  5. customthe solvent removed
  6. customto obtain the crude product as an off-white solid
  7. customFurther purification
  8. customby crystallization
  9. additionfrom a mixture of acetone (250 mL) and hexane (75 mL)

Sources & evidence

ORD record
ord-a227adb5584347019e9cf0455f838307
Source dataset
uspto-grants-1996_06
Patent number
US05527926

Linked notes

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