Reaktion #816438

Reaktionsgleichung

2-Butyl-5-(4-chlorophenyl)-4-hydroxyisothiazol-3(2H)-one 1,1-dioxide

DMF

oxalyl chloride

→

title compound

Ausbeute 87.0%

2-Butyl-4-chloro-5-(4-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide

Ausbeute 87.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then heated
2. 2
   Temperaturto reflux for 2 h
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto dry
5. 5
   workup.ADDITIONWater (30 mL) was added into the residue
6. 6
   ExtraktionIt was then extracted with DCM (20 mL×3)
7. 7
   Waschenwashed with water (50 mL×3) and brine (20 mL)
8. 8
   Trocknendried (MgSO4)
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was then purified by column chromatography (ISOLUTE SI, 20 g/70 mL)
11. 11
    Wascheneluting with DCM:heptane (25:75)

Vorschrift

2-Butyl-5-(4-chlorophenyl)-4-hydroxyisothiazol-3(2H)-one 1,1-dioxide (0.9 g, ca. 60%, 1.71 mmol) was dissolved in DCM (50 mL). DMF (0.13 mL) was added. Under nitrogen atmosphere, oxalyl chloride (0.434 g, 3.42 mmol) was dropped in. The mixture was then heated to reflux for 2 h and then evaporated to dry. Water (30 mL) was added into the residue. It was then extracted with DCM (20 mL×3). The extracts were combined and washed with water (50 mL×3) and brine (20 mL), dried (MgSO4) and evaporated. The residue was then purified by column chromatography (ISOLUTE SI, 20 g/70 mL), eluting with DCM:heptane (25:75), to give the title compound (0.496 g, 87%); 1H NMR (400 MHz, CDCl3): δ 7.93 (d, 2H), 7.54 (d, 2H), 3.76 (t; 2H), 1.85-1.77 (m, 2H), 1.48-1.39 (m, 2H), 0.98 (t, 3H); 13C NMR (100 MHz, CDCl3): δ 155.8, 142.4, 139.0, 130.2, 129.9, 127.7, 121.8, 40.8, 30.2, 19.9, 13.4.

Quelle