Hydrochloric Acid → 1-Benzyl-3-(3-iodophenyl)imidazolidine-2,4-dione

HRID 857131Notes

Reaction equation

HRID 857131 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+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C=O)C>[CH2:17]([N:10]1[CH2:11][C:12](=[O:13])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[C:9]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 218671043-(3-Iodophenyl)imidazolidine-2,4-dione

Product 1

HCID 218671811-Benzyl-3-(3-iodophenyl)imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-iodophenyl)imidazolidine-2,4-dione (1.7 g) in DMF (20 ml) was treated with sodium hydride (60% oil dispersion, 280 mg) and benzylchloride (1.93 ml) 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 petroleum ether-EtOAc (9:1 to 3:2) to give the title compound (1.38 g). LCMS RT=3.27 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 petroleum ether-EtOAc (9:1 to 3:2)

Sources & evidence

ORD record
ord-6bc0a221f63841f1b7aeb2c4e49e59bf
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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