Water → HCID 13577868, compound

HRID 483051Notes

Reaction equation

HRID 483051 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([OH:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[C:3]1=[O:16].[H-].[Na+].[CH2:19](Br)[CH3:20].O>CN(C)C=O>[CH3:1][N:2]1[CH2:6][CH:5]([O:7][CH2:19][CH3:20])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[C:3]1=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 133423223-(3,4-Dichlorophenyl)-4-hydroxy-1-methylimidazolidin-2-one

Product 1

HCID 13577868HCID 13577868, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

Dissolved in 100 ml of dimethylformamide was 10.4 g (0.04 mole) of 1-methyl-3-(3,4-dichlorophenyl)-4-hydroxyimidazolidine-2-one. The solution was cooled to 10° C. and 2 g (0.04 mole) of sodium hydride was added to the solution with stirring. After the addition, the mixture was stirred for 30 minutes and 4.4 g of ethyl bromide was added dropwise. The mixture was stirred at room temperature for 2 hours and water was added to the reaction mixture. The mixture was extracted with chloroform and the chloroform extract was concentrated, giving 9.5 g of an oil in 82.1% yield.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. extractionThe mixture was extracted with chloroform
  5. extractionthe chloroform extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-c841b01c86304c14844028d3f6d70b76
Source dataset
uspto-grants-1986_03
Patent number
US04578107

Reaction notes

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