[[(3-Nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester → 3-(3-Aminophenyl)imidazolidine-2,4-dione

HRID 1785310

Reaction equation

HRID 1785310 reaction equation
CO[C:3](=[O:18])[CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)=[O:7]>Cl.CC(C)=O>[NH2:15][C:11]1[CH:10]=[C:9]([N:8]2[C:3](=[O:18])[CH2:4][NH:5][C:6]2=[O:7])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 10934009[[(3-Nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester

Product 1

HCID 246884373-(3-Aminophenyl)imidazolidine-2,4-dioneYield 85.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A suspension of [[[(3-nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester (6.9 g, 27 mmol) in 6N aqueous hydrochloride solution (40 mL) and acetone (20 mL) was stirred at reflux overnight. The resulting solution was cooled and concentrated. The resulting yellowish suspension was filtered and the filter cake was washed with water (50 mL), aqueous sodium bicarbonate solution (50 mL), and air-dried to afford the title compound (4.4 g).

Workup

  1. temperatureat reflux overnight
  2. temperatureThe resulting solution was cooled
  3. concentrationconcentrated
  4. filtrationThe resulting yellowish suspension was filtered
  5. washthe filter cake was washed with water (50 mL), aqueous sodium bicarbonate solution (50 mL)
  6. customair-dried

Sources & evidence

ORD record
ord-79780408d8904b6aa7c78e70c80f72ef
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Linked notes

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