Potassium Carbonate → 1-(2-Chloropyrid-4-ylmethyl)-5,5-dimethyl-3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione

HRID 899958Notes

Reaction equation

HRID 899958 reaction equation
[CH3:1][C:2]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)=[O:9])([CH3:6])[C:3]([O-:5])=O.C([O-])([O-])=O.[K+].[K+].[Cl:28][C:29]1[CH:34]=[C:33]([CH2:35]Cl)[CH:32]=[CH:31][N:30]=1>CN(C=O)C>[Cl:28][C:29]1[CH:34]=[C:33]([CH2:35][N:7]2[C:2]([CH3:1])([CH3:6])[C:3](=[O:5])[N:10]([C:11]3[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[C:8]2=[O:9])[CH:32]=[CH:31][N:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 86595327HCID 86595327, compound

Product 1

HCID 545814241-(2-Chloropyrid-4-ylmethyl)-5,5-dimethyl-3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,5-Dimethyl-3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione 3 (1 g, 3.29 mmol) is dissolved in 10 ml of DMF, 1.36 g of K2CO3 (3 eq, 9.87 mmol) and 909 mg of 2-chloro-4-chloromethylpyridine (3.95 mmol, 1.2 eq) are added, and the mixture is refluxed for 20 hours. The solvent is removed under vacuum and the residue is dissolved in CH2Cl2 and treated three times with active charcoal. After removing the solvent, the product 1-(2-chloropyrid-4-ylmethyl)-5,5-dimethyl-3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione is obtained (3.2 g; 56%).

Workup

  1. temperaturethe mixture is refluxed for 20 hours
  2. customThe solvent is removed under vacuum
  3. dissolutionthe residue is dissolved in CH2Cl2
  4. additiontreated three times with active charcoal
  5. customAfter removing the solvent

Sources & evidence

ORD record
ord-057321be9bb54caca301af8150f9302c
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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