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

HRID 1862423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862423
[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-2e9abe8430f047f1b72d6303bbc1cca1
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06538004B2

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