N-bromobutanimide → 5-Bromo-2-(bromomethyl)-1,3-benzothiazole

HRID 415623

Reaktionsgleichung

Reaktionsgleichung von HRID 415623
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16]([CH3:18])=[N:15][C:14]=2[CH:19]=1>C(Cl)(Cl)(Cl)Cl>[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16]([CH2:18][Br:1])=[N:15][C:14]=2[CH:19]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 30174575-Bromo-2-methylbenzothiazole

Produkt 1

HCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazoleAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (4.45 g, 25 mmol, 1.4 equiv.) and subsequently α,α′azoisobutyronitrile (110 mg, 0.7 mmol, 0.04 equiv.) were added to a solution of 5-bromo-2-methyl-benzothiazole (4.07 g, 17.85 mmol, 1 equiv.) in CCl4 (110 ml). The reaction mixture was stirred at reflux for 24 hrs. After cooling, succinimide was removed by filtration and was rinsed with CCl4 (100 ml). The filtrate was evaporated to dryness under reduced pressure and the orange solid residue was purified by column chromatography on silica, eluted with CH2Cl2/hexane (20%-70% gradient), to give the desired product as a white solid, 2.15 g (39% yield). Mp 116-117, HPLC-MS (method 1): m/z 308 [M+H]+, Rt=4.84 min. The reaction gave also 1.40 g (20% yield) of the by-product 5-bromo-2-dibromomethyl-benzothiazole, as well as 0.89 g (22%) of un-reacted starting material.

Aufarbeitung

  1. temperatureat reflux for 24 hrs
  2. temperatureAfter cooling
  3. customsuccinimide was removed by filtration
  4. washwas rinsed with CCl4 (100 ml)
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe orange solid residue was purified by column chromatography on silica
  7. washeluted with CH2Cl2/hexane (20%-70% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9301f0f2d9c54f0d837119e98be88953
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088791B2

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