2,2-Dimethyl-1,3-dioxolane-4-carbonyl chloride → 3,5-Bis(2,2-dimethyl-1,3-dioxolane-4-carbamido)-2,4,6-triiodo-(2-acetoxyethyl)-benzene

HRID 1604192Notes

Reaction equation

HRID 1604192 reaction equation
[NH2:1][C:2]1[C:3]([I:17])=[C:4]([CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15])[C:5]([I:10])=[C:6]([NH2:9])[C:7]=1[I:8].[CH3:18][C:19]1([CH3:27])[O:23][CH:22]([C:24](Cl)=[O:25])[CH2:21][O:20]1>>[CH3:18][C:19]1([CH3:27])[O:23][CH:22]([C:24]([NH:9][C:6]2[C:5]([I:10])=[C:4]([CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15])[C:3]([I:17])=[C:2]([NH:1][C:24]([CH:22]3[CH2:21][O:20][C:19]([CH3:27])([CH3:18])[O:23]3)=[O:25])[C:7]=2[I:8])=[O:25])[CH2:21][O:20]1

Participants

3

Reactant 2

HCID 139748132,2-Dimethyl-1,3-dioxolane-4-carbonyl chlorideHCID 184291663,5-Diamino-2,4,6-triiodo-(2-acetoxyethyl)benzene

Product 1

HCID 867548663,5-Bis(2,2-dimethyl-1,3-dioxolane-4-carbamido)-2,4,6-triiodo-(2-acetoxyethyl)-benzeneYield 47%

Procedure

3,5-Diamino-2,4,6-triiodo-(2-acetoxyethyl)benzene was acylated with 2,2-dimethyl-1,3-dioxolane-4-carboxylic chloride (prepared in situ) according to the procedure in Example 29a. After work up, the product was purified by preparative HPLC and isolated in 47% yield.

Workup

  1. customAfter work up, the product was purified by preparative HPLC
  2. customisolated in 47% yield

Sources & evidence

ORD record
ord-947a1aa68747428594c741770946890f
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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