Sulfuryl chloride → 5-Bromo-2-chloro-1,3-benzothiazole

HRID 1965861Notes

Reaction equation

HRID 1965861 reaction equation
S(Cl)([Cl:4])(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13](S)=[N:12][C:11]=2[CH:16]=1>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([Cl:4])=[N:12][C:11]=2[CH:16]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178527757HCID 178527757, compound

Product 1

HCID 202512695-Bromo-2-chloro-1,3-benzothiazoleYield 100%

Procedure

To sulfuryl dichloride (5 mL) was added 5-bromobenzo[d]thiazole-2-thiol (450 mg, 1.8 mmol) portionwise. The mixture was stirred at rt for 1 hour and heated at 50° C. for 15 min. After cooling to rt, the reaction mixture was slowly poured onto ice (50 g) and the resulting suspension was stirred for 30 min. Solid was collected through filtration and washed with water (10 mL) and dried under high vacuum to afford 5-bromo-2-chlorobenzo[d]thiazole as a pink solid (470 mg, 100%). MS (ESI) m/z 248 (M+H+).

Workup

  1. temperatureheated at 50° C. for 15 min
  2. temperatureAfter cooling to rt
  3. additionthe reaction mixture was slowly poured onto ice (50 g)
  4. stirringthe resulting suspension was stirred for 30 min
  5. filtrationSolid was collected through filtration
  6. washwashed with water (10 mL)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-28443ae781844559a83c7081fbfc3abf
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

Loading…