Iodine → HCID 54423472, compound

HRID 343082Notes

Reaction equation

HRID 343082 reaction equation
[C:1]1([CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[C:9](=[N:11][OH:12])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[I-].[K+].II.[Al].S(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:10][C:9]1[C:8]([C:13]2[CH:14]=[CH:15][C:16]([S:19][CH3:20])=[CH:17][CH:18]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:12][N:11]=1

Participants

9

Reactant 6

HCID 807IodineHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 5359268AluminumHCID 23665763Sodium BisulfiteHCID 131721082HCID 131721082, compound

Product 1

HCID 54423472HCID 54423472, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-phenyl-2-(4-methylthiophenyl)-1-buten-3-one oxime (Step 2) (11.2 g, 0.0395 mol), sodium bicarbonate (13.6 g, 0.162 mol), and potassium iodide (22.95 g, 0.138 mol) in tetrahydrofuran (200 ml) and water (160 ml) was added iodine (10 g, 0.0395 mol). The reaction vessel was covered with aluminum foil and heated at reflux for 4 hours. Thin layer chromatography indicated the reaction was completed. The reaction was cooled to room temperature, sodium bisulfite was added and the reaction was extracted with ethyl acetate. The organic extracts were dried and the solvent was removed to give the crude isoxazole. The crude was purified by chromatography on silica gel using mixtures of ethyl acetate and toluene. The isoxazole was recrystallized from ethyl acetate and hexane to give pure compound as a crystalline solid (8.3 g, 75%): mp 88°-90° C. Anal. Calc'd. for C17H15NOS (281.38): C, 72.57; H, 5.37; N, 4.98; S, 11.40. Found: C, 72.20; H, 5.27; N, 4.58; S, 11.69.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. extractionthe reaction was extracted with ethyl acetate
  4. customThe organic extracts were dried
  5. customthe solvent was removed
  6. customto give the crude isoxazole
  7. customThe crude was purified by chromatography on silica gel using mixtures of ethyl acetate and toluene
  8. customThe isoxazole was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-d4e5ac77b2a04f55bf3e42e51f088616
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

Loading…