Reaktion #816430

Reaktionsgleichung

oxalyl chloride

Oxalyl chloride

2-Butyl-4-hydroxy-5-phenylisothiazol-3(2H)-one 1,1-dioxide

DMF

→

title compound

Ausbeute 92.9%

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

Ausbeute 92.9%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was refluxed for 1.5 h
2. 2
   Temperaturthe reaction mixture was refluxed for another 6 h
3. 3
   SonstigeThe solvents were evaporated
4. 4
   Sonstigethe residue was partitioned between water and DCM
5. 5
   WaschenThe combined organic layers were washed with water
6. 6
   Sonstigethe two phases were separated
7. 7
   SonstigeEvaporation of the organic phase

Vorschrift

2-Butyl-4-hydroxy-5-phenylisothiazol-3(2H)-one 1,1-dioxide (444 mg, 1.58 mmol) was dissolved in dry DCM (15 mL) at rt and under an atmosphere of nitrogen. Oxalyl chloride (0.15 mL, 1.73 mmol) was added dropwise and the reaction mixture was refluxed for 1.5 h. DMF (0.08 mL) was added followed by oxalyl chloride (0.15 mL, 1.73 mmol) in 2 portions and the reaction mixture was refluxed for another 6 h. The solvents were evaporated and the residue was partitioned between water and DCM. The combined organic layers were washed with water and the two phases were separated using a phase separator. Evaporation of the organic phase gave the title compound (440 mg, 88%) as a brown oil with approximately 95% purity according to 1H-NMR and was used without further purification; 1H-NMR (400 MHz, CDCl3): δ 7.96-8.00 (m, 2H), 7.53-7.62 (m, 3H), 3.74-3.80 (t, 2H), 1.78-1.87 (m, 2H), 1.39-1-50 (m, 2H), 0.98 (t, 3H); 13C-NMR (100 MHz, CDCl3): δ 156.3, 137.1, 132.7, 129.6, 129.2, 127.6, 123.7, 40.9, 30.1, 20.1, 13.7.

Quelle