2-Bromoethanol → HCID 86754526, compound

HRID 618929Notes

Reaction equation

HRID 618929 reaction equation
[I:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH:12]([OH:15])[CH2:13][OH:14])=[O:9])=[C:6]([I:16])[C:5]([C:17]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])=[O:18])=[C:4]([I:25])[C:3]=1[NH:26][C:27]([NH:29][C:30]1[C:35]([I:36])=[C:34]([C:37]([NH:39][CH2:40][CH:41]([OH:44])[CH2:42][OH:43])=[O:38])[C:33]([I:45])=[C:32]([C:46]([NH:48][CH2:49][CH:50]([OH:53])[CH2:51][OH:52])=[O:47])[C:31]=1[I:54])=[O:28].[OH-].[Na+].Br[CH2:58][CH2:59][OH:60]>O>[I:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH:12]([OH:15])[CH2:13][OH:14])=[O:9])=[C:6]([I:16])[C:5]([C:17]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])=[O:18])=[C:4]([I:25])[C:3]=1[N:26]([CH2:58][CH2:59][OH:60])[C:27]([NH:29][C:30]1[C:35]([I:36])=[C:34]([C:37]([NH:39][CH2:40][CH:41]([OH:44])[CH2:42][OH:43])=[O:38])[C:33]([I:45])=[C:32]([C:46]([NH:48][CH2:49][CH:50]([OH:53])[CH2:51][OH:52])=[O:47])[C:31]=1[I:54])=[O:28]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 21844899HCID 21844899, compound

Product 1

HCID 86754526HCID 86754526, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N'-bis[2,4,6-triiodo-3,5-bis(2,3-dihydroxypropylaminocarbonyl)phenyl]-urea (2.0 g, 1.4 mmol) was dissolved in water (13 ml) containing 2M NaOH (7 ml). 2-Bromoethanol (1 g, 8.4 mmol) was added and the mixture was stirred at ambient temperature for 60 h, treated with a strongly acidic ion exchange resin (Amberlyst 15) evaporated and purified by preparative HPLC. Yield: 1.45 g (70%) of the product as a white solid. 1H NMR (DMSO-d6): 9.10-9.38 (m, 1H, NH), 7.90-8.65 (m, 4H, NH), 3.02-3.91 (m, 24H).

Workup

  1. additiontreated with a strongly acidic ion exchange resin (Amberlyst 15)
  2. customevaporated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-436e533e33c3484c9059378d86d58d8b
Source dataset
uspto-grants-1999_09
Patent number
US05958375

Reaction notes

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