N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide → N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[(2-propenyloxy)acetyl]amino-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233066Notes

Reaction equation

HRID 233066 reaction equation
[CH2:1]([O:4][CH2:5][C:6](Cl)=[O:7])[CH:2]=[CH2:3].[C:9]([O:12][CH2:13][CH:14]([NH:20][C:21]([C:23]1[C:28]([I:29])=[C:27]([NH2:30])[C:26]([I:31])=[C:25]([C:32]([NH:34][CH:35]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:36][O:37][C:38](=[O:40])[CH3:39])=[O:33])[C:24]=1[I:46])=[O:22])[CH2:15][O:16][C:17](=[O:19])[CH3:18])(=[O:11])[CH3:10]>CN(C)C(=O)C>[C:43]([O:42][CH2:41][CH:35]([NH:34][C:32]([C:25]1[C:26]([I:31])=[C:27]([NH:30][C:6](=[O:7])[CH2:5][O:4][CH2:1][CH:2]=[CH2:3])[C:28]([I:29])=[C:23]([C:21]([NH:20][CH:14]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:13][O:12][C:9](=[O:11])[CH3:10])=[O:22])[C:24]=1[I:46])=[O:33])[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:45])[CH3:44]

Participants

4

Reactant 2

HCID 11766168N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamideHCID 13819389Allyloxyacetyl chloride

Product 1

HCID 10486105N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[(2-propenyloxy)acetyl]amino-2,4,6-triiodo-1,3-benzenedicarboxamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
5 °C

Procedure

Allyloxyacetyl chloride (9.0 g, 67 mmol) was added dropwise to a stirred solution of N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (30.0 g, 34 mmol) in N,N-dimethylacetamide (70 ml ) at 0°-5° C. The reaction mixture was stirred at 5° C. for 30 minutes and at room temperature for 20 hours. It was then slowly added dropwise to a well stirred mixture of ice-water (1.5 L), when a white solid separated out. This was collected by filtration, washed with water, and dried in vacuo to obtain N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[(2-propenyloxy)acetyl ]amino-2,4,6-triiodo-1,3-benzenedicarboxamide as a white amorphous solid (32.1 g, 97% yield), m.p. 214°-16°.

Workup

  1. additionIt was then slowly added dropwise to a well
  2. stirringstirred
  3. customseparated out
  4. filtrationThis was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4e814f58fd694820b406179dca2915d8
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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