Propylene Oxide → 1,3-Bis(2-hydroxypropyl)-5,5-dimethyl-2,4-imidazolidinedione

HRID 903333Notes

Reaction equation

HRID 903333 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Cl-].[Li+].[CH2:12]1[O:15][CH:13]1[CH3:14]>CN(C)C=O>[OH:15][CH:13]([CH3:12])[CH2:14][N:6]1[C:2]([CH3:9])([CH3:1])[C:3](=[O:8])[N:4]([CH2:12][CH:13]([OH:15])[CH3:14])[C:5]1=[O:7]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 6491DimethylhydantoinHCID 433294Lithium Chloride

Product 1

HCID 5506501,3-Bis(2-hydroxypropyl)-5,5-dimethyl-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 217 g of 5,5-dimethylhydantoin (1.695 mols) 3.61 g of lithium chloride (5 mol percent) and 560 ml of dimethylformamide is stirred at 50° C. 230 g of propene oxide (propylene oxide) (3.955 mols) are added dropwise to the clear solution over the course of 4 hours, 50°-55° C. The reaction is slightly exothermic. After the dropwise addition, the temperature is slowly raised to 90° C. After 5 hours at 90° C. the dimethylformamide is distilled off in a waterpump vacuum and thereafter the product is dried to constant weight at 100° C. and 0.1 mm Hg. 415 g of a pale yellow highly viscous oil (100% of theory) are obtained. The crude product is distilled at 0.1 to 0.2 mm Hg and 170°-172° C.: 386.0 g yield of pure material (93.5% of theory). On cooling the 1,3-di(β-hydroxy-n-propyl)- 5,5-dimethylhydantoin solidifies to give white crystals of melting point 65°-67° C. The elementary analysis shows 11.81% N (calculated, 11.47% N), and the molecular weight was determined by vapour pressure osmometry to be 247 (theory 244). The infrared spectrum shows the absence of N-H-amide frequencies at 3.1 to 3.2μ and the presence of C--OH frequencies at 2.90μ.

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe temperature is slowly raised to 90° C
  3. distillationAfter 5 hours at 90° C. the dimethylformamide is distilled off in a waterpump vacuum
  4. customthe product is dried to constant weight at 100° C.
  5. custom415 g of a pale yellow highly viscous oil (100% of theory) are obtained
  6. distillationThe crude product is distilled at 0.1 to 0.2 mm Hg and 170°-172° C.
  7. temperatureOn cooling the 1,3-di(β-hydroxy-n-propyl)- 5,5-dimethylhydantoin
  8. customto give white crystals of melting point 65°-67° C

Sources & evidence

ORD record
ord-a7acb556f3af40bc8103163f7c0111f4
Source dataset
uspto-grants-1980_10
Patent number
US04227005

Reaction notes

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