Potassium Iodide → HCID 13319880, compound

HRID 1248480Notes

Reaction equation

HRID 1248480 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[C:15](=[O:18])([OH:17])[O-].[Na+].[I-].[K+].[CH3:22][N:23]([CH3:26])C=[O:25]>>[C:8]([OH:7])(=[O:25])[C:15]([OH:17])=[O:18].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:23]3[CH2:26][CH2:5][CH2:4][CH2:3][CH2:2][CH2:22]3)=[N:6][O:7][C:8]=2[CH:13]=1

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13319880HCID 13319880, compoundYield 33%

Conditions

Temperature
80 °C

Procedure

To 40 ml of dry dimethylformamide, was added 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 2.3 ml of hexamethyleneimine, 8.0 g of sodium bicarbonate, and a crystal of potassium iodide. After stirring at 80° C. for three hrs, the mixture was filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 ml of water for five mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, the solvent was evaporated to an oil. The oil was treated with ethereal hydrogen chloride, and the resultant salt was recrystallized twice from ethylacetate/methanol/ether to give 2.4 g (33%) of product, mp 141°-142° C. (dec).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 ml of water for five mins
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water (2×), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvent was evaporated to an oil
  10. additionThe oil was treated with ethereal hydrogen chloride
  11. customthe resultant salt was recrystallized twice from ethylacetate/methanol/ether

Sources & evidence

ORD record
ord-22a86a95d0bf4732b5e8ae06a7454f5c
Source dataset
uspto-grants-1985_06
Patent number
US04524209

Reaction notes

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