Sodium hydride → 3-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one

HRID 1770725Notes

Reaction equation

HRID 1770725 reaction equation
[CH3:1][C:2]1([CH3:10])[NH:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[NH:3]1.[H-].[Na+].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22]OC1C=C(S([O-])(=O)=O)C=CC=1C>CN(C)C=O>[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:6]1[C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[NH:3][C:2]1([CH3:10])[CH3:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98127982,2,5,5-Tetramethyl-4-imidazolidinoneHCID 1317319672-[2-(2-Methoxyethoxy)ethoxy]ethoxy-p-toluenesulfonate

Product 1

HCID 675080933-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-oneYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2,5,5-Tetramethylimidazolidin-4-one (20.00 g, 140.6 mmol), prepared as described in U.S. Pat. No. 5,126,057 (Worely et al., Jun. 30, 1992), was dissolved in N,N-dimethylformamide (300 ml). To the stirring room temperature solution was added sodium hydride (60%, 5.06 g, 126.5 mmol), in 8 portions over 30 minutes. After an additional one hour of stirring at room temperature, [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]p-toluenesulfonate (40.15 g, 126.1 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 silica gel column chromatography (0 to 10% methanol in dichloromethane) to give 15.51 g (38%) of the title compound. 1H NMR (D2O, 400 MHz) δ 3.70-3.46 (m, 12H), 3.64-3.59 (m, 2H), 3.46 (t, J=6.2 Hz, 2H), 3.26 (s, 3H), 1.31 (s, 6H), 13C NMR (D2O, 100 MHz) δ 179.48, 76.22, 70.99, 69.59, 69.56, 69.39, 67.71, 58.90, 58.00, 39.70, 27.28, 25.67; LRMS (ESI/APCI) m/z 289 [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 silica gel column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7e9c91282d5143189307b68ad11d459b
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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