Sodium Iodide → N-[3-(iodoacetyl)-2-oxo-1-imidazolidinyl]carbamic acid, 1,1-dimethylethyl ester

HRID 4119Notes

Reaction equation

HRID 4119 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][N:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]1=[O:18])=[O:4].[I-:19].[Na+]>CC(C)=O>[I:19][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][N:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]1=[O:18])=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 57105682N-[3-(Bromoacetyl)-2-oxo-1-imidazolidinyl]carbamic acid, 1,1-dimethylethyl ester

Product 1

HCID 57241819N-[3-(iodoacetyl)-2-oxo-1-imidazolidinyl]carbamic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-[3-(Bromoacetyl)-2-oxo-1-imidazolidinyl]carbamic acid, 1,1-dimethylethyl ester (20.9 g, 65 mmol) was dissolved in acetone (250 ml) containing sodium iodide (10.5 g, 70 mmol). The solution was stirred at reflux for three hours and filtered hot through Celite. The solution was evaporated in vacuo to give the title compound as a light yellow solid, 23.9 g.

Workup

  1. temperatureat reflux for three hours
  2. filtrationfiltered hot through Celite
  3. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-71dd9c746bed41b09c643f7528bb9407
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Reaction notes

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