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Ethyl chloroformate → 4-[2-[2-Ethyl-4methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl-1,2,4-oxadiazolidine-3,5-dione

HRID 1602891
Notes
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Reaction equation

HRID 1602891 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:25]=[CH:24][C:17](CN(O)C(N)=O)=[CH:16][CH:15]=2)[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2].[OH-:26].[Na+].Cl[C:29]([O:31]CC)=[O:30]>O>[CH2:1]([C:3]1[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([N:8]3[C:29](=[O:30])[O:31][N:4]([CH3:5])[C:3]3=[O:26])=[CH:24][CH:25]=2)[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 21960191N-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzyl]-N-hydroxyurea

Product 1

HCID 867548014-[2-[2-Ethyl-4methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl-1,2,4-oxadiazolidine-3,5-dioneYield 76%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Conditions

Temperature
30 °C

Procedure

To a stirred solution of N-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzyl]-N-hydroxyurea (346 mg, 1.0 mmol) (obtained from preparation 19) in water (2 ml) was added 1N NaOH (3 ml) followed by ethyl chloroformate (191 μl, 217 mg, 2.0 mmol) and stirred for 1 h at 30° C. The reaction mixture was diluted with water, acidified to pH 3.0 and extracted with EtOAc (3×10 ml). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to yield the title compound (283 mg, 76%).

Workup

  1. extractionextracted with EtOAc (3×10 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c38d9960155e41d3a85482da91722cbb
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05985884

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes