Sodium hydride → HCID 57625984, compound

HRID 546575Notes

Reaction equation

HRID 546575 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]2=[O:21])[CH:5]=[CH:6][C:7]=1[S:8][C:9]([F:12])([F:11])[F:10].[H-].[Na+].[Cl:24][C:25]1[CH:30]=[C:29]([CH2:31]Cl)[CH:28]=[CH:27][N:26]=1>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:19])([CH3:20])[N:15]([CH2:31][C:29]3[CH:28]=[CH:27][N:26]=[C:25]([Cl:24])[CH:30]=3)[C:14]2=[O:21])[CH:5]=[CH:6][C:7]=1[S:8][C:9]([F:12])([F:10])[F:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 576260173-{3-Amino-4-[(trifluoromethyl)thio]phenyl}-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 57625984HCID 57625984, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 0.4 g of 3-{3-amino-4-[(trifluoro-methyl)thio]phenyl}-5,5-dimethylimidazolidine-2,4-dione obtained in stage c) below in 20 mL of dimethylformamide are added, under argon, 53 mg of 60% sodium hydride and stirring is continued for 20 minutes at room temperature. To this solution are added 2.85 g of 2-chloro-4chloromethylpyridine obtained in stage b) of Example 3 dissolved in 5 mL of dimethylformamide, and the reaction mixture is then heated at 70° C. for 3.5 hours and then poured into 100 mL of ice-water and extracted with three times 100 mL of ethyl acetate. The combined organic phases are dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is taken up in 100 mL of diethyl ether, washed with water, dried over magnesium sulphate, filtered and concentrated under vacuum to give 500 mg of 3-{3-amino-4-[(trifluoromethyl)thio]phenyl}-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. extractionextracted with three times 100 mL of ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2ab8142415bf4652a91608d60b034abe
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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