2-Bromoethanol → N,N'-bis[2,4,6-triiodo-3-(2-hydroxyethylaminocarbonyl)-5-(2,3-dihydroxypropylaminocarbonyl)phenyl]-N-hydroxyethylurea

HRID 618932Notes

Reaction equation

HRID 618932 reaction equation
[I:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][OH:13])=[O:9])=[C:6]([I:14])[C:5]([C:15]([NH:17][CH2:18][CH:19]([OH:22])[CH2:20][OH:21])=[O:16])=[C:4]([I:23])[C:3]=1[NH:24][C:25]([NH:27][C:28]1[C:33]([I:34])=[C:32]([C:35]([NH:37][CH2:38][CH:39]([OH:42])[CH2:40][OH:41])=[O:36])[C:31]([I:43])=[C:30]([C:44]([NH:46][CH2:47][CH2:48][OH:49])=[O:45])[C:29]=1[I:50])=[O:26].Br[CH2:52][CH2:53][OH:54]>O.[OH-].[Na+]>[I:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][OH:13])=[O:9])=[C:6]([I:14])[C:5]([C:15]([NH:17][CH2:18][CH:19]([OH:22])[CH2:20][OH:21])=[O:16])=[C:4]([I:23])[C:3]=1[N:24]([CH2:52][CH2:53][OH:54])[C:25]([NH:27][C:28]1[C:33]([I:34])=[C:32]([C:35]([NH:37][CH2:38][CH:39]([OH:42])[CH2:40][OH:41])=[O:36])[C:31]([I:43])=[C:30]([C:44]([NH:46][CH2:47][CH2:48][OH:49])=[O:45])[C:29]=1[I:50])=[O:26]

Participants

5

Reactant 2

HCID 108982-BromoethanolHCID 21844915N,N'-Bis[2,4,6-triiodo-3-(2-hydroxyethylaminocarbonyl)-5-(2,3-dihydroxypropylaminocarbonyl)-phenyl]urea

Product 1

HCID 86754528N,N'-bis[2,4,6-triiodo-3-(2-hydroxyethylaminocarbonyl)-5-(2,3-dihydroxypropylaminocarbonyl)phenyl]-N-hydroxyethylureaYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

N,N'-Bis[2,4,6-triiodo-3-(2-hydroxyethylaminocarbonyl)-5-(2,3-dihydroxypropylaminocarbonyl)-phenyl]urea (0.216 g, 0.157 mmol) was dissolved in a mixture of water (6 ml) and 2M aqueous NaOH (0.9 ml) together with 2-bromoethanol (0.067 ml). The mixture was stirred for 20 h, neutralized with a strongly acidic cation exchange resin and evaporated to dryness. Purification using preparative HPLC gave 105 mg (47%) of the product as a white solid.

Workup

  1. customevaporated to dryness
  2. customPurification

Sources & evidence

ORD record
ord-f9b62841e35045deb7319f8ab8abb397
Source dataset
uspto-grants-1999_09
Patent number
US05958375

Reaction notes

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