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

HRID 1846765Notes

Reaction equation

HRID 1846765 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-benzothiazoleYield 75%

Procedure

Sulfuryl chloride (0.3 mL, 4.41 mmol) was added neat to 5-fluoro-benzothiazole-2-thiol (680 mg, 3.67 mmol). The mixture was stirred at RT for 1 hour, and then heated to 60° C. for 40 mins. The resulting solution was cooled to room temperature, and poured onto ice, extracted with EtOAc (3×50 mL), washed with brine and dried over Na2SO4. The dried organic layers were concentrated to give 2-chloro-5-fluorobenzo[d]thiazole (520 mg, 2.75 mmol, 75%). ESI-MS (M+1): 187 calc. for C7H5ClFN4S 186.

Workup

  1. temperatureheated to 60° C. for 40 mins
  2. temperatureThe resulting solution was cooled to room temperature
  3. additionpoured onto ice
  4. extractionextracted with EtOAc (3×50 mL)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe dried organic layers were concentrated

Sources & evidence

ORD record
ord-36ecc8935dcb44c4ae4a047595363f23
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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