Water → 1-(4-Chlorobenzyl)-3-(2-methyl-2-oxiranylmethyl)imidazolidin-2-one

HRID 856127Notes

Reaction equation

HRID 856127 reaction equation
[H-].[Na+].C1(C)C=CC(S(O[CH2:13][C:14]2([CH3:17])[CH2:16][O:15]2)(=O)=O)=CC=1.[Cl:19][C:20]1[CH:32]=[CH:31][C:23]([CH2:24][N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])=[CH:22][CH:21]=1.O>CN(C=O)C>[Cl:19][C:20]1[CH:32]=[CH:31][C:23]([CH2:24][N:25]2[CH2:29][CH2:28][N:27]([CH2:13][C:14]3([CH3:17])[CH2:16][O:15]3)[C:26]2=[O:30])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 50764812-Imidazolidinone, 1-((4-chlorophenyl)methyl)-HCID 142371942-Methyloxiran-2-ylmethyl paratoluenesulfonate

Product 1

HCID 866047991-(4-Chlorobenzyl)-3-(2-methyl-2-oxiranylmethyl)imidazolidin-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (99 mg, 2.49 mmol) was added to a solution of 2-methyl-2-oxiranylmethyl toluene-4-sulfonate (500 mg, 2.37 mmol) in DMF (5 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 1 hour. To which a solution of 1-(4-chlorobenzyl)imidazolidin-2-one (633 mg, 2.61 mmol) in DMF (5 ml) was added while cooling in an ice-bath, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether twice. The extracts were combined, washed with water twice and then with brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/acetone=3/1) to afford 1-(4-chlorobenzyl)-3-(2-methyl-2-oxiranylmethyl)imidazolidin-2-one (399 mg, 60%) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. temperaturewhile cooling in an ice-bath
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with diethyl ether twice
  5. washwashed with water twice
  6. dry with materialwith brine, and dried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane/acetone=3/1)

Sources & evidence

ORD record
ord-ddd6fd6ea5c74b74a1315829a27ac8dc
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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