Acetoxyacetyl chloride → 5-(N-methylacetoxyacetylamino)-2,4,6-triiodo-isophthalic acid dichloride

HRID 223123Notes

Reaction equation

HRID 223123 reaction equation
C[NH:2][C:3]1[C:4]([I:17])=[C:5]([C:14]([Cl:16])=[O:15])[C:6]([I:13])=[C:7]([C:11]=1[I:12])[C:8]([Cl:10])=[O:9].[C:18]([O:21][CH2:22][C:23](Cl)=[O:24])(=[O:20])[CH3:19].[CH3:26]C(N(C)C)=O>>[CH3:26][CH2:19][C:18]([O:21][CH2:22][C:23]([NH:2][C:3]1[C:11]([I:12])=[C:7]([C:8]([Cl:10])=[O:9])[C:6]([I:13])=[C:5]([C:4]=1[I:17])[C:14]([Cl:16])=[O:15])=[O:24])=[O:20]

Participants

4

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 31374DimethylacetamideHCID 214667042,4,6-Triiodo-5-(methylamino)-1,3-benzenedicarbonyl dichloride

Product 1

HCID 887538585-(N-methylacetoxyacetylamino)-2,4,6-triiodo-isophthalic acid dichlorideYield 98.8%

Procedure

A solution of 32 g of 5-methylamino-2,4,6-triiodoisophthalic acid dichloride (0.0525 moles in 80 ml of DMAC is treated dropwise at 0° to 5° C. with stirring with 10.7 g of acetoxyacetylchloride. Subsequently, stirring is continued over night and at room temperature. The reaction solution is stirred into ice water. A total of 36.7 g of 5-(N-methylacetoxyacetylamino)-2,4,6-triiodo-isophthalic acid dichloride, melting at 198°-200° C., are obtained, corresponding to a theoretical yield of 98.8%.

Workup

  1. waitis continued over night and at room temperature

Sources & evidence

ORD record
ord-e75feeafe2844a9cb0383eae4fc8be2a
Source dataset
uspto-grants-1982_10
Patent number
US04352788

Reaction notes

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