Dimethylhydantoin → HCID 21395745, compound

HRID 1439504Notes

Reaction equation

HRID 1439504 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Cl-].[Li+].[CH3:12][CH2:13][CH:14]1[O:16][CH2:15]1>CN(C)C=O>[OH:16][CH:14]([CH2:13][CH3:12])[CH2:15][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 78341,2-EpoxybutaneHCID 433294Lithium Chloride

Product 1

HCID 21395745HCID 21395745, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

256.3 g of 5,5-dimethylhydantoin (2 mols) and 2.54 g of lithium chloride in 300 ml of dimethylformamide are together stirred at 65° C. 158.8 g of 1,2-butene oxide (2.2 mols) are slowly added dropwise over the course of 2 hours at this temperature. Thereafter the mixture is stirred for a further 4 hours at 100° C. The solution is cooled to room temperature and filtered, and the filtrate is then concentrated on a rotary evaporator at 70° C/20 mm Hg and dried to constant weight at 90° C/0.1 mm Hg. A crystalline, light yellow crude product is obtained in quantitative yield (400.1 g). The substance can be purified by recrystallisation from acetone. Colourless, glistening crystals melting at 87°-88.5° C are obtained.

Workup

  1. temperatureThe solution is cooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate is then concentrated on a rotary evaporator at 70° C/20 mm Hg
  4. customdried to constant weight at 90° C/0.1 mm Hg
  5. customA crystalline, light yellow crude product is obtained in quantitative yield (400.1 g)
  6. customThe substance can be purified by recrystallisation from acetone
  7. customare obtained

Sources & evidence

ORD record
ord-ef3aa97f6b8343cfa601a6a644ee0e23
Source dataset
uspto-grants-1977_11
Patent number
US04060525

Reaction notes

Loading…