HCID 10590086, compound → HCID 19362775, compound

HRID 850283Notes

Reaction equation

HRID 850283 reaction equation
[CH:1]([C:4]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:15]([CH3:17])[CH3:16])[C:5]=1[CH2:6]Br)([CH3:3])[CH3:2].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K]>CN(C)C=O>[CH:1]([C:4]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:15]([CH3:17])[CH3:16])[C:5]=1[CH2:6][N:22]1[C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]2[C:18]1=[O:28])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10590086HCID 10590086, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19362775HCID 19362775, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4,6-triisopropylbenzyl bromide (5.00 g, 16.8 mmol), potassium phthalimide (3.71 g, 19.9 mmol), and dimethylformamide were heated for 3 hours at 70° C. The reaction mixture was allowed to stand overnight at room temperature and was then heated at 90° C. for 1 hour. The solvent was removed on the rotary evaporator, ethyl acetate (250 mL) was added, the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to a white solid. Hexanes (50 mL) and ethyl acetate (5 mL) was added and the solid collected by filtration, 4.18 g (68%). An analytical sample was obtained by silica gel filtration using 9:1, hexanes/ethyl acetate as eluant.

Workup

  1. temperaturewas then heated at 90° C. for 1 hour
  2. customThe solvent was removed on the rotary evaporator, ethyl acetate (250 mL)
  3. additionwas added
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid
  8. additionHexanes (50 mL) and ethyl acetate (5 mL) was added
  9. filtrationthe solid collected by filtration, 4.18 g (68%)
  10. customAn analytical sample was obtained by silica gel filtration

Sources & evidence

ORD record
ord-ea6f98007f9d4872bc68f92d92723087
Source dataset
uspto-grants-2000_01
Patent number
US06017905

Reaction notes

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