Glycidol → HCID 67508091, compound

HRID 1770772Notes

Reaction equation

HRID 1770772 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+].[CH2:13]1[O:15][CH:14]1[CH2:16][OH:17]>CN(C)C=O>[OH:15][CH:14]([CH2:16][OH:17])[CH2:13][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 11164GlycidolHCID 24758Sodium hydrideHCID 98127982,2,5,5-Tetramethyl-4-imidazolidinone

Product 1

HCID 67508091HCID 67508091, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2,5,5-Tetramethylimidazolidin-4-one (3.54 g, 24.9 mmol), prepared as described in U.S. Pat. No. 5,126,057 (Worely et al., Jun. 30, 1992), was dissolved in N,N-dimethylformamide (150 ml). To the stirring room temperature solution was added sodium hydride (60%, 913 mg, 22.8 mmol), in 4 portions over 10 minutes. After an additional one hour of stirring at room temperature, the glycidol (1.4 ml, 21.1 mmol) was added to the reaction mixture. After the reaction mixture was stirred for 18 hours at room temperature, the mixture was concentrated in vacuo, and crude material is purified by silica gel column chromatography (0 to 20% methanol in dichloromethane) to give 250 mg (5%) the title compound.

Workup

  1. stirringAfter the reaction mixture was stirred for 18 hours at room temperature
  2. concentrationthe mixture was concentrated in vacuo, and crude material
  3. customis purified by silica gel column chromatography (0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9283b8ccf4424011a9ced877e7033dab
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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