Iodine → HCID 54567031, compound

HRID 342992Notes

Reaction equation

HRID 342992 reaction equation
[N+]([O-])(O)=O.[I:5]I.[CH:7]1([C:10]2[O:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[CH2:9][CH2:8]1>O>[CH:7]1([C:10]2[O:14][N:13]=[C:12]([CH3:15])[C:11]=2[I:5])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 807IodineHCID 944Nitric AcidHCID 10103167HCID 10103167, compound

Product 1

HCID 54567031HCID 54567031, compoundYield 211%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated nitric acid (10 ml) was added dropwise to a stirred heated mixture of iodine (23.8 g) and 5-cyclopropyl-3-methylisoxazole (24. 6 g containing approximately 20% 3-cyclopropyl-5-methylisoxazole) whilst maintaining the temperature in the range 90°-95° C. The mixture was stirred and heated at 95°-100° C. for 1 hour. It was cooled, poured into cold water and extracted with ether. The combined extracts were washed with aqueous sodium bicarbonate solution (saturated), aqueous sodium metabisulphate solution (saturated), water, dried over anhydrous sodium sulphate and filtered. The filtrate was evaporated to dryness and the residue was triturated with petroleum spirit and filtered. The solid was recrystallized from petroleum spirit to give 5-cyclopropyl-4-iodo-3-methylisoxazole (25.6 g) as a white solid, m.p. 71° C.

Workup

  1. temperatureheated
  2. temperaturewhilst maintaining the temperature in the range 90°-95° C
  3. temperatureheated at 95°-100° C. for 1 hour
  4. temperatureIt was cooled
  5. extractionextracted with ether
  6. washThe combined extracts were washed with aqueous sodium bicarbonate solution (saturated), aqueous sodium metabisulphate solution (saturated), water
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was triturated with petroleum spirit
  11. filtrationfiltered
  12. customThe solid was recrystallized from petroleum spirit

Sources & evidence

ORD record
ord-08e643b338574e0aaef5653ac32f52c1
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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