Azobisisobutyronitrile → 5-(Bromomethyl)-2,1,3-benzothiadiazole

HRID 1837066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837066
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[CH:3]=1.[Br:11]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[CH:3]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27812495-Methyl-2,1,3-benzothiadiazole

Produkt 1

HCID 5910045-(Bromomethyl)-2,1,3-benzothiadiazoleAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

5-Methylbenzo-2,1,3-thiadiazole (5 g, 33.3 mmol) in CHCl3 (75 mL) was treated with N-bromosuccinimide (5.32 g, 33.3 mmol) and a catalytic amount of AIBN and heated at reflux for 16 hours. After cooling to ambient temperature, the resulting precipitate was fitered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to provide 4.8 g of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.62 (s, 2H), 7.65 (dd, 1H), 8.0 (m, 2H).

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0254ffe7341c4f22ad77b9cb756393b8
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780872B2

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