Water → 1-[(3,4-Dichlorophenyl)methyl]imidazolidin-2-one

HRID 461525Notes

Reaction equation

HRID 461525 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:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:17]Cl.O>CS(C)=O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:17][N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 76093,4-Dichlorobenzyl chlorideHCID 84532-ImidazolidinoneHCID 11430Potassium Carbonate

Product 1

HCID 213940071-[(3,4-Dichlorophenyl)methyl]imidazolidin-2-oneYield 23%

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, 10.0 g (0.06 mole of KI and 49.0 g (0.25 mole) of 3,4-Dichlorobenzyl chloride. The reaction mixture was heated at 100° for 3 hours and poured into 1.8 1 of H2O. The aqueous mixture was extracted with 1.3 1 of chloroform. The chloroform extract was washed with 500 ml of H2O, dried over MgSO4 overnight and filtered. The filtrate was concentrated to dryness to give 14 g (23%) of a light yellow semisolid. The crude product was crystallized using 20 ml of acetonitrile, filtered, washed with ether, air dried and dried at 60° for 2 hrs to give 10.5 g (17%) of a white solid, m.p. 129°-130°. An analytical sample, m.p. 129°- 130°, was a portion of the above crystallized product.

Workup

  1. temperatureThe reaction mixture was heated at 100° for 3 hours
  2. extractionThe aqueous mixture was extracted with 1.3 1 of chloroform
  3. extractionThe chloroform extract
  4. washwas washed with 500 ml of H2O
  5. dry with materialdried over MgSO4 overnight
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-894fe34f554f4c14a6d83b114d3b5238
Source dataset
uspto-grants-1977_12
Patent number
US04063022

Reaction notes

Loading…