1-(3-Bromoprop-1-yl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidine → N-[3-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-1-propyl]phthalimide

HRID 602843Notes

Reaction equation

HRID 602843 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][CH2:15][CH2:16][N:17]1[Si:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][Si:18]1([CH3:25])[CH3:24]>CN(C)C=O>[CH3:22][Si:21]1([CH3:23])[CH2:20][CH2:19][Si:18]([CH3:25])([CH3:24])[N:17]1[CH2:16][CH2:15][CH2:14][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 42924111-(3-Bromoprop-1-yl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidineHCID 24194345Phthalimide potassium salt

Product 1

HCID 67079567N-[3-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-1-propyl]phthalimideYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

About 3.36 g of potassium phthalimide, 4.89 g of 1-(3-bromopropyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, and 12 mL of N,N-dimethylformamide were mixed in a flask. The mixture was stirred for 5 hour while the flask was kept in an oil bath maintained at 75° C. The N,N-dimethylformamide was removed under vacuum. The residue was extracted with 90 mL of toluene and filtered. The filtrate was evaporated under vacuum. The residue was triturated with 80 mL of hexane, cooled with dry ice, and then filtered to give N-[3-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-1-propyl]phthalimide (TMADSCPPI) as a white solid (4.3 g, 68% yield). 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product: δ 7.41 (multiplet, 2H, aromatic protons), 6.81 (multiplet, 2H, aromatic protons), 3.55 (multiplet, 2H, CH2 protons), 2.79 (multiplet, 2H, CH2 protons), 1.77 (multiplet, 2 H, CH2 protons), 0.70 (singlet, 4H, CH2—Si protons), 0.06 (singlet, 12H, Si—CH3 protons).

Workup

  1. customwas kept in an oil bath
  2. customThe N,N-dimethylformamide was removed under vacuum
  3. extractionThe residue was extracted with 90 mL of toluene
  4. filtrationfiltered
  5. customThe filtrate was evaporated under vacuum
  6. customThe residue was triturated with 80 mL of hexane
  7. temperaturecooled with dry ice
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1a3f10db70db4d87b5acae7267c965fd
Source dataset
uspto-grants-2011_03
Patent number
US07906592B2

Reaction notes

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