Potassium Iodide → HCID 13319880, compound
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]=1Participants
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
- filtrationthe mixture was filtered
- customthe filtrate was evaporated to an oil
- stirringThe oil was stirred with 100 ml of water for five mins
- extractionextracted with ether
- extractionThe ether extract
- washwas washed with water (2×), saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtering
- customthe solvent was evaporated to an oil
- additionThe oil was treated with ethereal hydrogen chloride
- customthe resultant salt was recrystallized twice from ethylacetate/methanol/ether
Sources & evidence
- ORD record
- ord-f869d712c3ed4f9f971f571c9798d921
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04598152
Reaction notes
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