1,3-Diiodo-5,5-dimethylimidazolidine-2,4-dione → 2-Iodo-6-methyl-2'-methylsulfinylbenzanilide

HRID 1828369Notes

Reaction equation

HRID 1828369 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([CH3:15])=[O:14])=[O:5].[I:20]N1C(C)(C)C(=O)N(I)C1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C(=O)C>[I:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:2]([CH3:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([CH3:15])=[O:14])=[O:5]

Participants

5

Reactant 2

HCID 2005341,3-Diiodo-5,5-dimethylimidazolidine-2,4-dioneHCID 220662302-Methyl-2'-methylsulfinylbenzanilide

Product 1

HCID 120105972-Iodo-6-methyl-2'-methylsulfinylbenzanilideYield 124%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

Into the same reactor as in Example 1 were charged 0.10 g of palladium acetate, 0.40 g of 2-methyl-2′-methylsulfinylbenzanilide, 0.33 g of 1,3-diiodo-5,5-dimethylhydantoin and 5 ml of N,N-dimethylacetamide. The mixture thus obtained was stirred at 90° C. for 2 hours. After cooling to room temperature, the reaction mixture was filtered with Celite, and the filtrate was poured into saturated aqueous solution of sodium thiosulfate and extracted with ethyl acetate. The organic layer was washed with 0.1N-aqueous hydrochloric acid and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The concentrate thus obtained was purified by silica gel dry column chromatography (hexane/ethyl acetate=1/2). Thus, 0.43 g (yield 72%) of 2-iodo-6-methyl-2′-methylsulfinylbenzanilide was obtained. Regioselectivity of iodination into the 2-position was 100%.

Workup

  1. customThe mixture thus obtained
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered with Celite
  4. additionthe filtrate was poured into saturated aqueous solution of sodium thiosulfate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 0.1N-aqueous hydrochloric acid
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. concentrationThe concentrate thus
  10. customobtained
  11. customwas purified by silica gel
  12. dry with materialdry column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-1c2b5db71560438e82d7af47107a815a
Source dataset
uspto-grants-2006_06
Patent number
US07057067B2

Reaction notes

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