Sulfuric Acid → 5,5-Dimethyl-3-(2-(vinyloxy)ethyl)imidazolidine-2,4-dione

HRID 1706284Notes

Reaction equation

HRID 1706284 reaction equation
OS(O)(=O)=O.[C:6]([O:9][CH:10]=[CH2:11])(=O)[CH3:7].OCC[N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[NH:17][C:16]1=[O:23]>C([O-])(=O)C.[Hg+]>[CH:10]([O:9][CH2:6][CH2:7][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[NH:17][C:16]1=[O:23])=[CH2:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7904Vinyl AcetateHCID 996053-(2-Hydroxyethyl)-5,5-dimethylhydantoin

Product 1

HCID 30179645,5-Dimethyl-3-(2-(vinyloxy)ethyl)imidazolidine-2,4-dioneYield 57.5%

Reagents, catalysts & solvents 1

HCID 61181Mercurous acetateCatalyst

Procedure

The same compound may also be obtained as follows: 0.3 g of H2SO4 is added dropwise, with vigorous stirring, to 400 ml of freshly distilled vinyl acetate, 0.002 g of Cu resinate and 0.96 g of mercury acetate, at -25° C., in a 1 liter round-bottomed flask. 41.4 g of 3-hydroxyethyl-5,5-dimethyl-hydantoin are then added, with brief stirring, under conditions such that the temperature in the flask does not rise above -20°. The resulting dispersion is kept at a temperature between -20° C. and -30° C., with slow stirring, and after 16 hours the undissolved alcohol (5.2 g) is filtered off, the solution is poured into ice water which contains sufficient sodium carbonate that the pH value resulting after addition of the solution is 8 or above, and finally the organic phase is separated from the aqueous phase, washed twice with water, dried over sodium sulphate and concentrated on a rotary evaporator. 27.4 g (= 57.5% of theory) of 3-vinyloxyethyl-5,5-dimethyl-hydantoin are obtained.

Workup

  1. customThe same compound may also be obtained
  2. customdoes not rise above -20°
  3. customis kept at a temperature between -20° C. and -30° C., with slow stirring
  4. filtrationafter 16 hours the undissolved alcohol (5.2 g) is filtered off
  5. additionthe solution is poured into ice water which
  6. customresulting
  7. additionafter addition of the solution
  8. customabove, and finally the organic phase is separated from the aqueous phase
  9. washwashed twice with water
  10. dry with materialdried over sodium sulphate
  11. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-7939b926c3284b37bca8a88807790161
Source dataset
uspto-grants-1980_06
Patent number
US04206309

Reaction notes

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