반응 #816438

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

DMF

oxalyl chloride

→

title compound

수율 87.0%

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

수율 87.0%

용매

DCM

반응 조건

후처리

1. 1
   온도The mixture was then heated
2. 2
   온도to reflux for 2 h
3. 3
   기타evaporated
4. 4
   기타to dry
5. 5
   workup.ADDITIONWater (30 mL) was added into the residue
6. 6
   추출It was then extracted with DCM (20 mL×3)
7. 7
   세척washed with water (50 mL×3) and brine (20 mL)
8. 8
   건조dried (MgSO4)
9. 9
   기타evaporated
10. 10
    기타The residue was then purified by column chromatography (ISOLUTE SI, 20 g/70 mL)
11. 11
    세척eluting with DCM:heptane (25:75)

실험 절차

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.

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