Dimethylhydantoin → HCID 18976545, compound

HRID 2393667Notes

Reaction equation

HRID 2393667 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19]Br>CN(C)C=O>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 18976545HCID 18976545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

85.46 g (0.667 mol) of 5,5-dimethylhydantoin, 110.6 g (0.80 mol) of anhydrous potassium carbonate and 124.0 g (0.7336 mol) of 2-bromoacetaldehyde dimethyl acetal in 600 ml of dimethylformamide are reacted for about 6 hours analogously to Example 1 in a glass apparatus. The reaction mixture is subsequently cooled to room temperature and filtered with suction, the filtrate is evaporated in a rotary evaporator, and the residue is dried at 110° C./0.1 mbar. The crude yield is 143.2 g (99.3% of theory) of 3-(2,2-dimethoxyethyl)-5,5-dimethylimidazolidine-2,4-dione. 21 g of the crude product are dissolved in 50 ml of 0.1N sodium hydroxide solution at room temperature, and the solution is extracted 3 times by shaking with 30 ml of tert-butyl methyl ether in each case in a separating funnel. The organic phases are combined, the solution is dried using anhydrous sodium sulfate and subsequently filtered, the clear filtrate is evaporated in a rotary evaporator, and the residue is dried for 1 hour at 60° C./0.1 mbar, giving 12.3 g of pure, highly viscous 3-(2,2-dimethoxyethyl)-5,5-dimethylimidazolidine-2,4-dione having the following analytical data:

Workup

  1. filtrationfiltered with suction
  2. customthe filtrate is evaporated in a rotary evaporator
  3. customthe residue is dried at 110° C./0.1 mbar
  4. dissolution21 g of the crude product are dissolved in 50 ml of 0.1N sodium hydroxide solution at room temperature
  5. extractionthe solution is extracted 3 times
  6. customthe solution is dried
  7. filtrationsubsequently filtered
  8. customthe clear filtrate is evaporated in a rotary evaporator
  9. customthe residue is dried for 1 hour at 60° C./0.1 mbar

Sources & evidence

ORD record
ord-fe023f053e92468f95305627be3f0bb4
Source dataset
uspto-grants-1998_09
Patent number
US05807927

Reaction notes

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