Sulfuryl chloride → 4-Chloro-2,3-dihydro-1,2-benzothiazol-3-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11]C)[C:3]=1/[CH:4]=[N:5]/O.S(Cl)(Cl)(=O)=[O:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[C:4](=[O:14])[NH:5][S:11][C:7]=2[CH:8]=[CH:9][CH:10]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
(E)-2-Chloro-6-(methylthio)benzaldehyde oxime (12.37 g) was dissolved in toluene (35 mL). Sulfuryl chloride (5.4 ml, 66.24 mmol) was added, dropwise to the solution at 0° C., followed by heating at 80° C. for 1 h. After the completion of the reaction, the reaction mixture was cooled to room temperature and a white precipitate formed. The solid was collected by vacuum filtration, washed with toluene and air dried to 4-chlorobenzo[d]isothiazol-3(2H)-one (6 g). (This method is general for other 2-(methythio) benzaldehyde oximes.) 1H NMR (300 MHz, DMSO-d6): 7.90 (t, 1H), 7.55 (t, 1H), 7.41 ppm (d, 1H). MW=186 confirmed by LC-MS, tr=2.38 min (Method B) MH+=187.