1,3-Diiodo-5,5-dimethylimidazolidine-2,4-dione → HCID 12010618, compound

HRID 1828374Notes

Reaction equation

HRID 1828374 reaction equation
[I:1]N1C(C)(C)C(=O)N(I)C1=O.[CH3:12][C:13]([NH:19][C:20]([C:22]1[CH:34]=[CH:33][CH:32]=[CH:31][C:23]=1[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])=[O:21])([CH3:18])[CH2:14][S:15]([CH3:17])=[O:16]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C(=O)C>[CH3:12][C:13]([NH:19][C:20]([C:22]1[C:34]([I:1])=[CH:33][CH:32]=[CH:31][C:23]=1[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])=[O:21])([CH3:18])[CH2:14][S:15]([CH3:17])=[O:16]

Participants

5

Reactant 2

HCID 2005341,3-Diiodo-5,5-dimethylimidazolidine-2,4-dione2×HCID 22066222n-Butyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)benzoate

Product 1

HCID 12010618HCID 12010618, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

Into the same reactor as in Example 1 were charged 1.32 mg of palladium acetate, 0.78 g of 1,3-diiodo-5,5-dimethylhydantoin, n-butyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)benzoate and 5 ml of N,N-dimethylacetamide. After stirring the mixture at 90° C. for 30 minutes, 0.56 g of 1,3-diiodo-5,5-dimethylhydantoin was added, and the mixture thus obtained was stirred at 90° C. for 3.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, an aqueous solution of sodium thiosulfate was added, and the mixture thus obtained was extracted twice with toluene. The organic layer was washed successively with 0.5N aqueous hydrochloric acid, an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product thus obtained was washed with hexane-ether mixture to obtain 2.26 g of n-butyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)-3-iodobenzoate (yield 82%, melting point 57.5–66.3° C.). Regioselectivity of iodination into the 3-position was 100%.

Workup

  1. customthe mixture thus obtained
  2. stirringwas stirred at 90° C. for 3.5 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionan aqueous solution of sodium thiosulfate was added
  6. customthe mixture thus obtained
  7. extractionwas extracted twice with toluene
  8. washThe organic layer was washed successively with 0.5N aqueous hydrochloric acid
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe crude product thus obtained
  12. washwas washed with hexane-ether mixture

Sources & evidence

ORD record
ord-2f1474381eee49b4a599b4598fcd4ae1
Source dataset
uspto-grants-2006_06
Patent number
US07057067B2

Reaction notes

Loading…