Sulfuryl chloride → 2-Chloro-5-(trifluoromethyl)-1,3-benzothiazole

HRID 907714Notes

Reaction equation

HRID 907714 reaction equation
S(Cl)([Cl:4])(=O)=O.S[C:7]1[S:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:10]=2[N:11]=1>>[Cl:4][C:7]1[S:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:10]=2[N:11]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiol

Product 1

HCID 219858492-Chloro-5-(trifluoromethyl)-1,3-benzothiazoleYield 94%

Procedure

Sulfuryl chloride (9.09 g, 67.33 mmol) was added with stirring to 2-mercapto-5-(trifluoromethyl)benzothiazole (2.64 g, 11.22 mmol) over a period of 5 minutes. The reaction mixture was then allowed to stand for approximately 1 h. Ice water was added to the reaction mixture with stirring to decompose the excess of sulfuryl chloride, and the product was then extracted with ethyl acetate. The organic layer was washed with water (3×) and brine, dried over anhydrous Na2SO4 and concentrated. The resulting solid was dissolved in EtOAc and filtered though a short silica-gel column, eluting with EtOAc, to give 2-chloro-5-(trifluoromethyl)benzothiazole (2.50 g, 94%). LC-MS m/z 238.0 (MH+), ret. time 2.55 min; 1H NMR (400 MHz, DMSO-d6) δ 7.81 (d, 1H), 8.38 (m, 2H).

Workup

  1. extractionthe product was then extracted with ethyl acetate
  2. washThe organic layer was washed with water (3×) and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. dissolutionThe resulting solid was dissolved in EtOAc
  6. filtrationfiltered though a short silica-gel column
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-887b5af0f343422fb931930366c800a7
Source dataset
uspto-grants-2011_09
Patent number
US08013166B2

Reaction notes

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