N-bromobutanimide → 3-Bromo-s-triazolo(3,4-b)benzothiazole

HRID 461849

Reaktionsgleichung

Reaktionsgleichung von HRID 461849
[N:1]1[N:2]=[CH:3][N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=12.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][C:3]1[N:4]2[C:5]([S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=32)=[N:1][N:2]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 2545687-Thia-2,4,5-triazatricyclo(6.4.0.0,2,6)dodeca-1(12),3,5,8,10-pentaene

Produkt 1

HCID 213928313-Bromo-s-triazolo(3,4-b)benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

s-Triazolo(3,4-b)benzothiazole (6.4 grams; 0.0366 mole) was slurried with 200 milliliters of carbon tetrachloride, with stirring, at room temperature, and then heated. N-Bromosuccinimide (6.8 grams; 0.0366 mole plus 5 percent) was added and the solution refluxed and a pinch of azobisisobutylnitrile added to initiate the reaction. Subsequently the reaction mixture was filtered to separate blackish crystals, which were washed with carbon tetrachloride. The carbon tetrachloride was removed by evaporation, to yield a purple solid. This was chromatographed on a column packed with silica gel and eluted with ethyl acetate. The second portion was analyzed by elemental analysis and NMR, which confirmed its identity as the expected 3-bromo-s-triazolo(3,4-b)benzothiazole, m.p., 166°-7° C.

Aufarbeitung

  1. temperatureheated
  2. temperaturethe solution refluxed
  3. customthe reaction
  4. filtrationSubsequently the reaction mixture was filtered
  5. customto separate blackish crystals, which
  6. washwere washed with carbon tetrachloride
  7. customThe carbon tetrachloride was removed by evaporation
  8. customto yield a purple solid
  9. customThis was chromatographed on a column
  10. washeluted with ethyl acetate
  11. customm.p., 166°-7° C.

Quellen und Nachweise

ORD-Eintrag
ord-713f96a82a5f4e89add3b978835770c7
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04064261

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