Potassium Iodide → HCID 13319848, compound

HRID 745315Notes

Reaction equation

HRID 745315 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.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[C:20](=[O:23])([OH:22])[O-].[Na+].[I-].[K+].CN(C)C=[O:30]>>[C:8]([OH:7])(=[O:30])[C:20]([OH:22])=[O:23].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:6][O:7][C:8]=2[CH:13]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13319848HCID 13319848, compoundYield 44%

Conditions

Temperature
70 °C

Procedure

To 50 ml of dry dimethylformamide, was added 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 5.0 ml of pyrrolidine, 8.0 g of sodium bicarbonate, and a crystal of potassium iodide. After stirring at 70° C. for four 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 oxalic acid, and the resultant salt was recrystallized twice from ethyl acetate/methanol/ether to give 2.7 g, (44%) of product, mp 190°-200° 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 oxalic acid
  11. customthe resultant salt was recrystallized twice from ethyl acetate/methanol/ether

Sources & evidence

ORD record
ord-5ed5a5ab955e40f58e7a5c2e11388e6c
Source dataset
uspto-grants-1986_07
Patent number
US04598152

Reaction notes

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