Propylene Oxide → HCID 20327279, compound

HRID 259395Notes

Reaction equation

HRID 259395 reaction equation
[CH2:1]([N:11]1[C:17]([CH3:19])([CH3:18])[C:15](=[O:16])[NH:14][C:12]1=[O:13])[N:2]1[C:8]([CH3:10])([CH3:9])[C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH2:20]1[O:23][CH:21]1[CH3:22]>[Cl-].[Li+].CN(C)C=O>[CH2:1]([N:2]1[C:8]([CH3:10])([CH3:9])[C:6](=[O:7])[N:5]([CH2:20][CH:21]([OH:23])[CH3:22])[C:3]1=[O:4])[N:11]1[C:17]([CH3:19])([CH3:18])[C:15](=[O:16])[N:14]([CH2:20][CH:21]([OH:23])[CH3:22])[C:12]1=[O:13]

Participants

5

Reactant 2

HCID 6378Propylene OxideHCID 7167651,1'-methylenebis(5,5-dimethylimidazolidine-2,4-dione)

Product 1

HCID 20327279HCID 20327279, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 433294Lithium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 268.3 g of 1,1'-methylene-bis-(5,5-dimethylhydantoin) [1 mol], 600 ml of dimethylformamide and 2.11 g of lithium chloride is stirred at 60° C. 134.0 g of propene oxide (2.3 mols) are slowly added dropwise to this mixture over the course of 1 hour and 45 minutes. Thereafter the mixture is heated to 100° C. over the course of 1.5 hours and stirred at 100° C. for a further 2 hours. The hot reaction mixture is now filtered and cooled to room temperature, neutralized with 20% strength sulphuric acid and concentrated to dryness on a rotary evaporator. The crude product is recrystallised from ethanol. 327.0 g of pure 1,1'-methylene-bis-(3-β-hydroxy-n-propyl-5,5-dimethylhydantoin) [85.3% of theory] of melting point 131°-133° C. are obtained. Microanalysis shows 14.50% N (calculated, 14.58% N); analysis by gel permeation chromatography shows that the substance is of uniform molecular weight. The N--NMR (nuclear magnetic resonance) spectrum and the IR (infrared) spectrum can be reconciled with the following structure: ##STR9##

Workup

  1. temperatureThereafter the mixture is heated to 100° C. over the course of 1.5 hours
  2. stirringstirred at 100° C. for a further 2 hours
  3. filtrationThe hot reaction mixture is now filtered
  4. temperaturecooled to room temperature
  5. concentrationconcentrated to dryness on a rotary evaporator
  6. customThe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-ac95d5a30de44e79b5920a0a65a73ead
Source dataset
uspto-grants-1977_07
Patent number
US04038277

Reaction notes

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