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

HRID 461849

Reaction equation

HRID 461849 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-713f96a82a5f4e89add3b978835770c7
Source dataset
uspto-grants-1977_12
Patent number
US04064261

Linked notes

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