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Hydrochloric Acid → 2-[3-(3-Iodophenyl)-2,4-dioxoimidazolidin-1-yl]acetamide

HRID 857122
Notes
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Reaction equation

HRID 857122 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][NH:10][C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:18][C:19]([NH2:21])=[O:20].Cl>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][N:10]([CH2:18][C:19]([NH2:21])=[O:20])[C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 218671043-(3-Iodophenyl)imidazolidine-2,4-dione

Product 1

HCID 218671362-[3-(3-Iodophenyl)-2,4-dioxoimidazolidin-1-yl]acetamideYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of 3-(3-iodophenyl)imidazolidine-2,4-dione (1 g) in DMF (20 ml) was treated with sodium hydride (60% oil dispersion, 158 mg) and 2-bromoacetamide (1.36 g) at 20° C. After 2 h the reaction mixture was treated with aqueous 2M HCl, extracted with EtOAc and dried (MgSO4). The solvent was removed under reduced pressure and the residue was purified by chromatography on Biotage (40 g) eluting with EtOAc to give the title compound (638 mg). LCMS RT=2.32 min.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by chromatography on Biotage (40 g)
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-0253ce75f86c4ad0ba150c9855cc5e5d
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07144908B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes