Sodium Iodide → HCID 19786553, compound

HRID 1646724Notes

Reaction equation

HRID 1646724 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:19](=[O:20])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C)C=O>[CH3:21][C:22]1[N:23]([CH2:2][CH2:3][CH2:4][CH:5]2[C:19](=[O:20])[C:9]3[C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][O:12][C:8]=3[CH2:7][CH2:6]2)[CH:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 127492-MethylimidazoleHCID 81531DiisopropylethylamineHCID 19786584HCID 19786584, compound

Product 1

HCID 19786553HCID 19786553, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
76 °C

Procedure

To a solution consisting of 5-(3-chloropropyl)-6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one (5.80 g) and dimethylformamide (57.0 ml) was added 2-methylimidazole (3.30 g), diisopropylethyl amine (10.5 ml) and sodium iodide (9.04 g) at room temperature with stirring. The reaction was flushed with nitrogen and warmed at 76° C. for 1 hour. Upon cooling to room temperature, dilute aqueous sodium bicarbonate and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous layer extracted twice with ethyl acetate and once with ether. The combined organic layers were washed with brine and concentrated to give the crude product. Drying was accomplished by azeotroping with benzene. Purification via flash column chromatography (silica gel, 2% triethylamine/0-20% methanol/ether) afforded 2.70 g (40%) of 6,7-dihydro-5-[3-(2-methyl-1H-imidazol-1-yl)-propyl]-3-phenyl-1,2-benzisoxazol-4(5H)-one. Recrystallization from dichloromethane/ether/pentane gave the product, m.p. 97°-99° C.

Workup

  1. customThe reaction was flushed with nitrogen
  2. temperatureUpon cooling to room temperature
  3. additiondilute aqueous sodium bicarbonate and ethyl acetate were added to the reaction mixture
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted twice with ethyl acetate and once with ether
  6. washThe combined organic layers were washed with brine
  7. concentrationconcentrated
  8. customto give the crude product
  9. customDrying
  10. customby azeotroping with benzene
  11. customPurification via flash column chromatography (silica gel, 2% triethylamine/0-20% methanol/ether)

Sources & evidence

ORD record
ord-08e0b853f72e48bcb7ee833d18be5c24
Source dataset
uspto-grants-1993_01
Patent number
US05180834

Reaction notes

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