Reaktion #816432

Reaktionsgleichung

DMF

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

Oxalyl chloride

→

title compound

Ausbeute 92.7%

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

Ausbeute 92.7%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturto reflux for 2.5 h
3. 3
   SonstigeThe reaction mixture was evaporated to dryness
4. 4
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
5. 5
   Waschenit was washed with several portions of water
6. 6
   Trocknendried with MgSO4
7. 7
   Sonstigeevaporated

Vorschrift

Dry DMF (0.17 mL, 2.21 mmol) was added to a solution of 2-butyl-5-(3-chlorophenyl)-4-hydroxyisothiazol-3(2H)-one 1,1-dioxide (697 mg, 2.21 mmol) in dry DCM (15 mL) at rt and under an atmosphere of nitrogen. Oxalyl chloride (0.37 mL, 4.41 mmol) was added dropwise and the mixture was heated to reflux for 2.5 h. The reaction mixture was evaporated to dryness. The residue was dissolved in EtOAc and it was washed with several portions of water, dried with MgSO4, and evaporated to give the title compound (685 mg, 84%) as a brown oil which was used without further purification; 1H NMR (500 MHz, CDCl3): δ 7.96 (t, 1H), 7.84-7.88 (m, 1H), 7.57-7.61 (m, 1H), 7.50-7.55 (t, 1H), 3.79 (t, 2H), 1.80-1.87 (m, 2H), 1.39-1.51 (m, 2H), 1.00 (t, 3H); 13C NMR (125 MHz, CDCl3): δ 161.5, 155.9, 142.4, 135.8, 132.8, 131.0, 129.0, 127.3, 125.1, 41.0, 30.4, 20.1, 13.7.

Quelle