Carbon Tetrachloride → 6-Bromomethyl-2-cyclohexyl-benzothiazole

HRID 911327

Reaktionsgleichung

Reaktionsgleichung von HRID 911327
[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:25][CH2:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([CH:1]3[CH2:2][CH2:7][CH2:6][CH2:5][CH2:4]3)[S:9][C:10]=2[CH:16]=1

Komponenten

6

Edukt 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 508498892-Benzyl-6-methyl-benzothiazole

Produkt 1

HCID 576564066-Bromomethyl-2-cyclohexyl-benzothiazoleAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Combine 2-benzyl-6-methyl-benzothiazole (0.6 g, 2.42 mmol), NBS (0.5 g, 2.54 mmol), AIBN (40 mg, 0.24 mmol), carbon tetrachloride (10 mL) and reflux for 3 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the organic extracts over anhydrous Na2SO4, concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the title compound as a white solid (0.4 g, 53%). MS (ES+) m/z: 311 (M+H)+.

Aufarbeitung

  1. washwash with water
  2. dry with materialDry the organic extracts over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-bfa01b655c134fa38693c1c683fbef7f
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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