Hydrochloric Acid → 3-(3-Iodophenyl)imidazolidine-2,4-dione

HRID 857105Notes

Reaction equation

HRID 857105 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][CH2:12][C:13]([O:15]CC)=O)=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:15])[CH2:12][NH:11][C:9]2=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 21867094Ethyl N-{[(3-iodophenyl)amino]carbonyl}glycinate

Product 1

HCID 218671043-(3-Iodophenyl)imidazolidine-2,4-dioneYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl N-{[(3-iodophenyl)amino]carbonyl}glycinate (9.42 g) in DMF (60 ml) was treated with sodium hydride (60% oil dispersion, 1.2 g) at 20° C. After 2 h the reaction mixture was treated with aqueous 2M HCl (200 ml) and stirred overnight. The solid was collected by filtration, washed with water and dried to give the title compound (6.9 g) LCMS RT=2.45 min.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-64023520ea564a86a19be31abc8c1cae
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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