Iodine → HCID 54567031, compound

HRID 266550Notes

Reaction equation

HRID 266550 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 109.6%

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 coming 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-f70b9c81587d4641b325e4953ea7148a
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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