Water → 1-(2,6-Dichlorobenzyl)-2-imidazolidinone

HRID 1580123Notes

Reaction equation

HRID 1580123 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:15]=1[CH2:16]Cl.O>CS(C)=O>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:15]=1[CH2:16][N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 748322,6-Dichlorobenzyl chloride

Product 1

HCID 215651751-(2,6-Dichlorobenzyl)-2-imidazolidinoneYield 21%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 21.5 g (0.25 mole) portion of 2-imidazolidinone in 250 ml of dimethylsulfoxide was treated with 34.5 g (0.25 mole) of K2CO3, 20 g (0.12 mole) of KI and 48.9 g (0.25 mole) of 2,6-dichlorobenzyl chloride. The reaction mixture was heated to 105° over 0.3 hours, held at 105° for 1.7 hours and poured into 1.5 l of water all with rapid stirring. The aqueous mixture was extracted with 1.3 l of chloroform. The chloroform extract was washed with 500 ml of water, dried over MgSO4 overnight and filtered. The filtrate was concentrated under reduced pressure leaving %) 48 g (79(of a light yellow viscous oil. The crude product was crystallized using 125 ml of ether, filtered, air dried and dried to a constant weight at 60° to give 13 g (21%) of a white solid m.p. 156°-158°.

Workup

  1. temperatureThe reaction mixture was heated to 105° over 0.3 hours
  2. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  3. extractionThe chloroform extract
  4. washwas washed with 500 ml of water
  5. dry with materialdried over MgSO4 overnight
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customleaving %) 48 g (79(of a light yellow viscous oil
  9. customThe crude product was crystallized
  10. filtrationfiltered
  11. customair dried
  12. customdried to a constant weight at 60°

Sources & evidence

ORD record
ord-eafe77ffa2c24b50b6a019ae41def633
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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