Propylene Oxide → 1,3-Di-(beta-hydroxy-n-propyl)-5-isopropylhydantoin

HRID 971906Notes

Reaction equation

HRID 971906 reaction equation
[CH:1]([CH:4]1[NH:8][C:7](=[O:9])[NH:6][C:5]1=[O:10])([CH3:3])[CH3:2].[Cl-].[Li+].[CH2:13]1[O:16][CH:14]1[CH3:15]>OS(O)(=O)=O.CN(C)C=O>[OH:16][CH:14]([CH3:13])[CH2:15][N:8]1[CH:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:10])[N:6]([CH2:13][CH:14]([OH:16])[CH3:15])[C:7]1=[O:9]

Participants

6

Reactant 3

HCID 6378Propylene OxideHCID 1030335-IsopropylhydantoinHCID 433294Lithium Chloride

Product 1

HCID 233382101,3-Di-(beta-hydroxy-n-propyl)-5-isopropylhydantoin

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 995.0 g of 5-isopropylhydantoin (7 mols), 2000 ml of dimethylformamide and 14.8 g of lithium chloride is stirred at 50° C. 1220 g of propene oxide (21 mols) are slowly added dropwise over the course of 6 hours. Thereafter the temperature is gradually raised at 70° C. and after a total of 15 hours the reaction mixture is allowed to cool. It is adjusted to pH = 7 with a few drops of 2 N H2SO4 and the pale yellow solution is filtered. The solution is completely concentrated at 90° C. bath temperature on a rotational evaporator under a waterpump vacuum and is subsequently treated at 90° C./0.1 mm Hg until constant weight is reached. 1654.5 g of a pale yellow highly viscous product (91.7% of theory) are obtained.

Workup

  1. temperatureThereafter the temperature is gradually raised at 70° C.
  2. customafter a total of 15 hours
  3. temperatureto cool
  4. filtrationthe pale yellow solution is filtered
  5. concentrationThe solution is completely concentrated at 90° C. bath temperature
  6. customon a rotational evaporator under a waterpump vacuum
  7. additionis subsequently treated at 90° C./0.1 mm Hg until constant weight
  8. custom1654.5 g of a pale yellow highly viscous product (91.7% of theory) are obtained

Sources & evidence

ORD record
ord-50303a5f2b1542f0b179e4164ad806e7
Source dataset
uspto-grants-1979_07
Patent number
US04161594

Reaction notes

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