반응 #816430

반응 방정식

oxalyl chloride

Oxalyl chloride

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

DMF

→

title compound

수율 92.9%

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

수율 92.9%

용매

DCM

반응 조건

후처리

1. 1
   온도the reaction mixture was refluxed for 1.5 h
2. 2
   온도the reaction mixture was refluxed for another 6 h
3. 3
   기타The solvents were evaporated
4. 4
   기타the residue was partitioned between water and DCM
5. 5
   세척The combined organic layers were washed with water
6. 6
   기타the two phases were separated
7. 7
   기타Evaporation of the organic phase

실험 절차

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.

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