Acetoxyacetyl chloride → 5-[[2-(Acetyloxy)acetyl]amino]-2,4,6-triiodo-1,3-benzenedicarbonyl dichloride

HRID 1645500Notes

Reaction equation

HRID 1645500 reaction equation
[NH2:1][C:2]1[C:3]([I:16])=[C:4]([C:13]([Cl:15])=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8].[C:17]([O:20][CH2:21][C:22](Cl)=[O:23])(=[O:19])[CH3:18]>CC(N(C)C)=O>[Cl:9][C:7]([C:6]1[C:10]([I:11])=[C:2]([NH:1][C:22]([CH2:21][O:20][C:17](=[O:19])[CH3:18])=[O:23])[C:3]([I:16])=[C:4]([C:13]([Cl:15])=[O:14])[C:5]=1[I:12])=[O:8]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichloride

Product 1

HCID 129431915-[[2-(Acetyloxy)acetyl]amino]-2,4,6-triiodo-1,3-benzenedicarbonyl dichloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

5-Amino-2,4,6-triiodo-isophthaloyl dichloride was dissolved in dimethyl acetamide (DAMC) and a solution of acetoxyacetylchloride (2 eq) in DMAc was slowly added with efficient stirring. The reaction mixture was stirred overnight and the following day, the mixture was slowly poured into stirred ice water. The precipitate was filtered off and dried to give the desired material. The structure was confirmed by 1H NMR (CDCl3, 300 MHz): 10.43 (brs, 1H); 4.71 (s, 2H); 2.11 (s, 3H)

Workup

  1. additionthe following day, the mixture was slowly poured
  2. filtrationThe precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-b97a9d610b804cbcbdc5a07d1a9c0b68
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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