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

HRID 9575

Reaktionsgleichung

Reaktionsgleichung von HRID 9575
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

Komponenten

3

Edukt 2

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d12c540085124d09aa48e1da1b1b4a13
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091228B2

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