Sulfuryl chloride → 2-Chloro-5-fluoro-1,3-benzothiazole

HRID 30888Notes

Reaction equation

HRID 30888 reaction equation
S(Cl)([Cl:4])(=O)=O.[F:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13](S)=[N:12][C:11]=2[CH:16]=1>>[Cl:4][C:13]1[S:14][C:10]2[CH:9]=[CH:8][C:7]([F:6])=[CH:16][C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178419066HCID 178419066, compound

Product 1

HCID 112408962-Chloro-5-fluoro-1,3-benzothiazole

Procedure

Sulfuryl chloride (50 μL, 0.65 mmol) was added neat to 5-fluoro-1,3-benzothiazole-2-thiol (100 mg, 0.54 mmol). The mixture was stirred at ambient temperature for 1 h, then heated at 60° C. for 30 minutes. The resulting solution was cooled to rt, and poured onto ice. The title compound was collected by filtration, washed with water, and dried under vacuum. The solid obtained was used without further purification; LC-MS m/z 188.1 (MH+), ret. time 3.27 min.

Workup

  1. temperatureheated at 60° C. for 30 minutes
  2. temperatureThe resulting solution was cooled to rt
  3. additionpoured onto ice
  4. filtrationThe title compound was collected by filtration
  5. washwashed with water
  6. customdried under vacuum
  7. customThe solid obtained
  8. customwas used without further purification

Sources & evidence

ORD record
ord-818e8828137b49d1a0afa27e7b262d3e
Source dataset
uspto-grants-2008_09
Patent number
US07423156B2

Reaction notes

Loading…