Iodine → HCID 54068353, compound

HRID 1289463Notes

Reaction equation

HRID 1289463 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][O:15][CH3:16])[C:8](=[O:17])[C:7](=[O:18])[NH:6]2.S(=O)(=O)(O)O.[I:26](O)(=O)=O.II>C(O)(=O)C.O>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[I:26])[N:9]([CH2:13][CH2:14][O:15][CH3:16])[C:8](=[O:17])[C:7](=[O:18])[NH:6]2

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24345Iodic acidHCID 4589432HCID 4589432, compound

Product 1

HCID 54068353HCID 54068353, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

288 mg of 6-trifluoromethyl-1-(1-methoxyeth-2-yl)-1,2,3,4-tetrahydro-2,3-dioxoquinoxaline is mixed in 5 ml of glacial acetic acid with 0.05 ml of water, 0.012 ml of concentrated sulfuric acid, 34.4 mg of iodic acid and 88.4 mg of iodine and heated for 4 hours to 80° C. After concentration by evaporation, it is taken up in water, adjusted alkaline and extracted with methylene chloride. The organic phase is dried, filtered and concentrated by evaporation and the residue is chromatographed on silica gel with toluene:glacial acetic acid:water=10:10:1 as eluant. 40 mg of 6-trifluoromethyl-7-iodo-1-(1-methoxyeth-2-yl)-1,2,3,4-tetrahydro-2,3-dioxoquinoxaline is obtained. The residue is starting material, which can be used again in the reaction.

Workup

  1. temperatureheated for 4 hours to 80° C
  2. concentrationAfter concentration
  3. customby evaporation, it
  4. extractionextracted with methylene chloride
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customthe residue is chromatographed on silica gel with toluene

Sources & evidence

ORD record
ord-cd404630da9d4ebb95649d28c43027fc
Source dataset
uspto-grants-1998_05
Patent number
US05750525

Reaction notes

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