Propylene Oxide → 1-(2-Hydroxypropyl)-3-(2-vinyloxyethyl)-5,5-dimethylhydantoin

HRID 127670Notes

Reaction equation

HRID 127670 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]1=[O:14])=[CH2:2].[CH2:15]1[O:18][CH:16]1[CH3:17].[Cl-].[Li+]>CN(C)C=O>[OH:18][CH:16]([CH3:17])[CH2:15][N:8]1[C:9]([CH3:13])([CH3:12])[C:10](=[O:11])[N:6]([CH2:5][CH2:4][O:3][CH:1]=[CH2:2])[C:7]1=[O:14]

Participants

5

Reactant 3

HCID 6378Propylene Oxide2×HCID 433294Lithium ChlorideHCID 30179645,5-Dimethyl-3-(2-(vinyloxy)ethyl)imidazolidine-2,4-dione

Product 1

HCID 202856301-(2-Hydroxypropyl)-3-(2-vinyloxyethyl)-5,5-dimethylhydantoin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

297 g (1.5 mols) of 3-(2-vinyloxyethyl)-5,5-dimethylhydantoin, prepared as described in Example 1, 87 g (1.5 mols) of propylene oxide, 7.5 g of lithium chloride and 750 ml of dimethylformamide are allowed to react for 4 hours and 30 minutes at 90°-112° C. A further 83.5 g (1.44 mols) of propylene oxide are then added dropwise in the course of 3 hours and 30 minutes at 112°-113° C. and the mixture is left to react for a further 15 minutes. It is then concentrated on a rotary evaporator at 80° C. under vacuum from a waterpump and dried to constant weight at 80° C. and 13.3 Pa. 382 g (99.6% of theory) of a brown, clear, viscous crude product are obtained and are purified by distillation. 347.7 g (90.4 g) of a clear, colourless distillate boiling at 149°-152° C./13.3 Pa are obtained.

Workup

  1. customto react for 4 hours and 30 minutes at 90°-112° C
  2. waitthe mixture is left
  3. customto react for a further 15 minutes
  4. concentrationIt is then concentrated on a rotary evaporator at 80° C. under vacuum from a waterpump
  5. customdried to constant weight at 80° C.
  6. custom382 g (99.6% of theory) of a brown, clear, viscous crude product are obtained
  7. distillationare purified by distillation
  8. custom347.7 g (90.4 g) of a clear, colourless distillate boiling at 149°-152° C./13.3 Pa are obtained

Sources & evidence

ORD record
ord-65b29a96631d4a738b7604a3cc95f790
Source dataset
uspto-grants-1981_03
Patent number
US04256867

Reaction notes

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