Ethyl chloroacetate → 1-(3-Iodophenyl)-2,4-imidazolidinedione

HRID 857103Notes

Reaction equation

HRID 857103 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:15][C:16](OCC)=[O:17]>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:15][C:16](=[O:17])[NH:11][C:9]2=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 21867173(3-iodophenyl)urea

Product 1

HCID 218671771-(3-Iodophenyl)-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodophenylurea (2.1 g) in DMF (20 ml) was treated with sodium hydride (60% oil dispersion; 640 mg), followed by ethyl chloroacetate (0.93 ml) and the mixture was stirred for 5 h. The mixture was partitioned between EtOAc and 2M HCl and the organic solution was washed with NaHCO3, brine, dried and evaporated to dryness to give the title compound (2.08 g) ES+ve 303(MH)+.

Workup

  1. customThe mixture was partitioned between EtOAc and 2M HCl
  2. washthe organic solution was washed with NaHCO3, brine
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b5db57e3fd204cacb9fdda816d0786a8
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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