Chlorotrimethylsilane → N-(2,6-Dimethylbenzyl)phthalimide

HRID 1911626Notes

Reaction equation

HRID 1911626 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4]O.Cl[Si](C)(C)C.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CS(C)=O.CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][N:20]1[C:16](=[O:26])[C:17]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:18]2[C:19]1=[O:21]

Participants

8

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 186748(2,6-Dimethylphenyl)methanolHCID 24194345Phthalimide potassium salt

Product 1

HCID 10825581N-(2,6-Dimethylbenzyl)phthalimide

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 2,6-Dimethylbenzyl Alcohol (Step A, 6.59 g, 48.4 mmol) in DMSO (20 ml) was added chlorotrimethylsilane (15.75 ml, 145 mmol) at room temperature, and the mixture was stirred for one hr. To this reaction mixture were added ethyl acetate and water, the organic layer washed with brine, dried over Na2SO4, filtered and concentrated to give an oil. The oily residue was redissolved in DMF (100 ml) and potassium phthalimide (10.76 g, 58.1 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature, ethyl acetate was added, and the organic layer was washed with 3% Na2CO3, 1 N HCl, dried over Na2SO4, filtered and concentrated to give white solid. The purification was done by flash chromatography on silica gel column (chloroform:methanol 95:5) to provide the title compound as white solid.

Workup

  1. washthe organic layer washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oil
  6. stirringThe reaction mixture was stirred for 16 hours at room temperature
  7. washthe organic layer was washed with 3% Na2CO3, 1 N HCl
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give white solid
  12. customThe purification

Sources & evidence

ORD record
ord-0c652af077c5479daf732a307d9ebceb
Source dataset
uspto-grants-2013_12
Patent number
US08604083B2

Reaction notes

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