Thionyl Chloride → 2,6,7-Trichloro-benzothiazole

HRID 598515Notes

Reaction equation

HRID 598515 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](S)[S:8][C:4]=2[C:3]=1[Cl:12].S(Cl)([Cl:15])=O>CN(C)C=O>[Cl:15][C:7]1[S:8][C:4]2[C:3]([Cl:12])=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1785277912(3H)-Benzothiazolethione, 6,7-dichloro-

Product 1

HCID 577488542,6,7-Trichloro-benzothiazoleYield 41.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 300 mg (1.270 mmol) 6,7-dichloro-benzothiazole-2-thiol in 1.4 mL (19.05 mmol) thionyl chloride was added dropwise 32.3 □L N,N-dimethylformamide dry at room temperature. The mixture was stirred at room temperature for 4 h. The solvent was removed in vacuo. The residue was purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 127 mg (41.9%) of the title compound as a yellow solid. MS(m/e): 239 (M+H+).

Workup

  1. customdry at room temperature
  2. customThe solvent was removed in vacuo
  3. customThe residue was purified with flash column chromatography on silica eluting with a gradient
  4. customformed from n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-ffb89a1d559d41edb66e5f362008ee1e
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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