Methylurea → 1-Methylimidazolidine-2,4,5-trione

HRID 76333

Reaction equation

HRID 76333 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].[C:6](Cl)(=[O:10])[C:7](Cl)=[O:8]>O1CCCC1.O>[CH3:1][N:2]1[C:7](=[O:8])[C:6](=[O:10])[NH:5][C:3]1=[O:4]

Participants

5

Reactant 2

HCID 11719MethylureaHCID 65578Oxalyl chloride

Product 1

HCID 1231961-Methylimidazolidine-2,4,5-trioneYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 1-methylurea (200 mg, 2.70 mmol) in dry tetrahydrofuran (6 mL) was added oxalyl chloride (0.26 mL, 2.97 mmol) dropwise, under a nitrogen atmosphere. The reaction mixture was stirred at 0-5° for 2 h and then allowed to warm to room temperature for 1 h before being diluted with water. The product was extracted with ethyl acetate, and the extracts were washed with water, dried and evaporated to give the product as an off-white solid (326 mg, 94%), mp 146-149° C. (lit. 145-148° C.).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe extracts were washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5270f0fd388c4422b4413078322e13df
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Linked notes

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