Dimethylhydantoin → 3-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 1770727Notes

Reaction equation

HRID 1770727 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[H-].[Na+].[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21]OC1C=C(S([O-])(=O)=O)C=CC=1C>CN(C)C=O>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][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 24758Sodium hydrideHCID 1317319672-[2-(2-Methoxyethoxy)ethoxy]ethoxy-p-toluenesulfonate

Product 1

HCID 675100513-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dioneYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,5-Dimethylhydantoin (1.32 g, 10.3 mmol) was dissolved in N,N-dimethylformamide (100 ml). To the stirring room temperature solution was added sodium hydride (60%, 412 mg, 10.2 mmol). After an additional one hour of stirring at room temperature, [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]p-toluenesulfonate (3.28 g, 10.3 mmol) was slowly added to the basic solution over a 20 minute period. The reaction mixture was stirred for an additional 18 hours at room temperature. The reaction mixture was concentrated under high vacuum. The solid material was dissolved in dichloromethane and the solution was filtered to remove any solid material. The organic layer was concentrated in vacuo, and crude material was purified by preparative-high pressure liquid chromatography to give 900 mg (31%) of the title compound. 1H NMR (D2O, 400 MHz) δ 3.56-3.51 (m, 12H), 3.37 (s, 3H), 1.42 (s, 6H); LRMS (ESI/APCI) m/z 275 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred for an additional 18 hours at room temperature
  2. concentrationThe reaction mixture was concentrated under high vacuum
  3. dissolutionThe solid material was dissolved in dichloromethane
  4. filtrationthe solution was filtered
  5. customto remove any solid material
  6. concentrationThe organic layer was concentrated in vacuo, and crude material
  7. customwas purified by preparative-high pressure liquid chromatography

Sources & evidence

ORD record
ord-480e5cb3eebc4e98a8f3ec5899d07aab
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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