Azobisisobutyronitrile → 4-Bromomethyl-1-ethyl-3-(2-trimethylsilanylethoxymethyl)-1,3-dihydrobenzimidazol-2-one

HRID 1176614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176614
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=2[N:5]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1=[O:21])[CH3:2].[Br:22]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:12][C:11]1[C:6]2[N:5]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:18])[CH3:20])[C:4](=[O:21])[N:3]([CH2:1][CH3:2])[C:7]=2[CH:8]=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68499694HCID 68499694, Verbindung

Produkt 1

HCID 685034284-Bromomethyl-1-ethyl-3-(2-trimethylsilanylethoxymethyl)-1,3-dihydrobenzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

The mixture of 1.00 g of 1-ethyl-4-methyl-3-(2-trimethylsilanylethoxymethyl)-1,3-dihydrobenzimidazol-2-one, 0.469 g of N-bromosuccinimide, 0.025 g of 2,2′-azobis(2-methylpropionitrile) and 0.037 g of dibenzoyl peroxide in 60 ml of carbon tetrachloride is heated to reflux with stirring. The reaction vessel is irradiated with a 150 W lamp over the reaction time. After 0.5 hour, the reaction mixture is cooled and filtered through Hyflo. The filtrate is concentrated. The title compound is obtained as a yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (40:1 dichloromethane-diethyl ether); Rt=5.80.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux
  3. customThe reaction vessel is irradiated with a 150 W lamp over the reaction time
  4. temperaturethe reaction mixture is cooled
  5. filtrationfiltered through Hyflo
  6. concentrationThe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-336e1af8fe5b4df38041b6d407270ce0
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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