Phosphate → HCID 21867081, compound

HRID 857128Notes

Reaction equation

HRID 857128 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1.Br[CH2:16][C:17]([NH2:19])=[O:18].[H-].[Na+].P([O-])([O-])([O-])=O>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C:11](=[O:13])[N:10]([CH2:16][C:17]([NH2:19])=[O:18])[C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 218671771-(3-Iodophenyl)-2,4-imidazolidinedione

Product 1

HCID 21867081HCID 21867081, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Iodophenyl)imidazolidine-2,4-dione (0.302 g) was taken up in dry DMF (15 ml) and treated with bromoacetamide (0.399 g) and then with sodium hydride (60% oil dispersion, 48 mg). After 3 h pH 6.4 phosphate buffer (50 ml) was added and the reaction mixture extracted with EtOAc (3×25 ml), dried (MgSO4) and evaporated under reduced pressure. Thee residue was purified by Flash chromatography (Merck 9385, EtOAc then 9:1 EtOAc:MeOH) to give the title compound (0.279 g). LCMS RT=2.62 min.

Workup

  1. extractionthe reaction mixture extracted with EtOAc (3×25 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThee residue was purified by Flash chromatography (Merck 9385, EtOAc

Sources & evidence

ORD record
ord-d4a1e396c3324e4a9b75a0480149c796
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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