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

HRID 2427352Notes

Reaction equation

HRID 2427352 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-510f2995051d46efb90bc6f3d4bdb130
Source dataset
uspto-grants-2011_06
Patent number
US07968576B2

Reaction notes

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