Potassium Iodide → 2-Imidazolidinone, 1-((4-chlorophenyl)methyl)-

HRID 1658818Notes

Reaction equation

HRID 1658818 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CS(C)=O.O>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:1]2[CH2:5][CH2:4][NH:3][C:2]2=[O:6])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 84532-ImidazolidinoneHCID 11430Potassium Carbonate

Product 1

HCID 50764812-Imidazolidinone, 1-((4-chlorophenyl)methyl)-Yield 92%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A 21.5 g (0.25 mole) portion of 2-imidazolidinone in 300 ml of dimethylsulfoxide was treated with 34.5 g (0.25 mole) of potassium carbonate, 10 g (0.06 mole) of potassium iodide and 40.5 g (0.25 mole) of 4-chlorobenzyl chloride. The reaction mixture was heated to 100° over 0.3 hours, held at 100° with rapid stirring for 1.3 hours and poured into 1.3 l of water. The aqueous mixture was extracted with 1.3 l of chloroform. The chloroform extract was washed with 150 ml of water, dried over magnesium sulfate for 3 hours and filtered. The filtrate was concentrated to dryness to give 49 g (92%) a light yellow oil which crystallized.

Workup

  1. temperatureThe reaction mixture was heated to 100° over 0.3 hours
  2. customheld at 100°
  3. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  4. extractionThe chloroform extract
  5. washwas washed with 150 ml of water
  6. dry with materialdried over magnesium sulfate for 3 hours
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-6b90fcd9ea3c4192b711a5f5685fe479
Source dataset
uspto-grants-1976_06
Patent number
US03966758

Reaction notes

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