Water → HCID 10857002, compound

HRID 2226994Notes

Reaction equation

HRID 2226994 reaction equation
[OH-].[K+].[NH:3]1[CH2:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[CH2:10]([O:17][CH2:18]Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(C(C)=O)C(C)C.COCCOCCN(CCOCCOC)CCOCCOC>[CH2:10]([O:17][CH2:18][N:5]1[C:6](=[O:8])[CH2:7][NH:3][C:4]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10006HydantoinHCID 14797Potassium HydroxideHCID 137983Benzyl chloromethyl ether

Product 1

HCID 10857002HCID 10857002, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-CatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

In 5 ml of methyl isobutyl ketone were suspended 216 mg (3.85 mmoles) of potassium hydroxide and 73 mg (0.226 mmoles) of tris[2-(2-methoxyethoxy)ethyl]-amine followed by addition of 900 mg (8.99 mmoles) of imidazolidine-2,4-dione, and the mixture was stirred at room temperature for 10 minutes. Then, 704 mg (4.50 mmoles) of benzyloxymethyl chloride was added dropwise at 0° C. and the mixture was stirred at room temperature for 3 hours. To this reaction mixture was added water and the organic layer was separated and washed successively with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was subjected to silica gel chromatography (eluent: hexane:ethyl acetate =1:1) to give 687 mg (3.12 mmoles) of 3-benzyloxymethylimidazolidine-2,4-dione. Yield 70% (based on benzyloxymethyl chloride) 1H-NMR, δ(CDCl3): 3.90 (2H, s), 4.60 (2H, s), 5.05 (2H, s), 6.00-6.20 (1H, brs, -NH), 7.20-7.45 (5H, m)

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customthe organic layer was separated
  3. washwashed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-3a0c7ad92686481eab2d1eeb84d24593
Source dataset
uspto-grants-1994_09
Patent number
US05350859

Reaction notes

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