Sulfuryl chloride → 2-Chloro-6-trifluoromethylbenzothiazole

HRID 9577Notes

Reaction equation

HRID 9577 reaction equation
S[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.S(Cl)([Cl:18])(=O)=O>>[Cl:18][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178418874HCID 178418874, compound

Product 1

HCID 114704192-Chloro-6-trifluoromethylbenzothiazoleYield 91%

Procedure

Sulfuryl chloride (40 mL) was added with stirring to 2-mercapto-6-(trifluoromethyl)-benzothiazole (18.0 g, 76.7 mmol) at <20° C. under a nitrogen atmosphere, and the suspension was then stirred at rt for 2 h. The reaction mixture was poured into ice water with stirring. Precipitation was formed, and stirring was continued for 2 h. The solid precipitate was filtered, and rinsed with water. The wet filter cake was dissolved in 100 mL EtOAc, and the solution was washed with 100 mL water and 50 mL saturated aqueous NaHCO3 solution, then dried over Na2SO4. EtOAc was removed by rotary evaporation, and the residue was dried in vacuo to afford the desired product as a light yellow solid (16.5 g, 91%). GC-EIMS m/z 237 (M+); 1H NMR (CDCl3) δ 8.10 (s, 1 H), 8.00 (d, 1 H), 7.70 (d, 1 H).

Workup

  1. stirringwith stirring
  2. customPrecipitation
  3. customwas formed
  4. stirringstirring
  5. waitwas continued for 2 h
  6. filtrationThe solid precipitate was filtered
  7. washrinsed with water
  8. dissolutionThe wet filter cake was dissolved in 100 mL EtOAc
  9. washthe solution was washed with 100 mL water and 50 mL saturated aqueous NaHCO3 solution
  10. dry with materialdried over Na2SO4
  11. customEtOAc was removed by rotary evaporation
  12. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-dff72be06ffa49d882790277e1d786cf
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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