Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloro-4-(chloromethyl)pyridine | HCID 11126573 | — |
| Reactant | 3-{3-Amino-4-[(trifluoromethyl)thio]phenyl}-5,5-dimethylimidazolidine-2,4-dione | HCID 57626017 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57625984 | HCID 57625984 | 89.7% |
Reaction Steps
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:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07935819B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-2ab8142415bf4652a91608d60b034abe |
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| Source note | uspto-grants-2011_05 |
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