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 602843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602843
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 67079567N-[3-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-1-propyl]phthalimideAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1a3f10db70db4d87b5acae7267c965fd
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906592B2

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