تفاعل #657293

معادلة التفاعل

sodium carbonate

3-(3,4′-dichloro-5-methyl-biphenyl-4-yl)-4-hydroxy-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]dec-3-en-2-one

sodium hydrogen carbonate

sulfuryl chloride

→

3-Chloro-3-(3,4′-dichloro-5-methyl-biphenyl-4-yl)-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]decane-2,4-dione

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers were separated
2. 2
   استخلاصthe water phase extracted with ethyl acetate (3×20 ml)
3. 3
   غسيلthe combined organic phases washed with saturated aqueous sodium carbonate and brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 2:1)

الإجراء التجريبي

To a solution of 3-(3,4′-dichloro-5-methyl-biphenyl-4-yl)-4-hydroxy-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]dec-3-en-2-one (100 mg, 0.224 mmol) and sodium hydrogen carbonate (47 mg, 0.560 mmol) in dichloromethane (5 ml) at −5° C. was added sulfuryl chloride (0.017 ml, 28.3 mg, 0.210 mmol) in dichloromethane (0.5 ml) dropwise. The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature overnight, poured on saturated aqueous sodium carbonate, the layers were separated, the water phase extracted with ethyl acetate (3×20 ml), the combined organic phases washed with saturated aqueous sodium carbonate and brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 2:1). Yield: 65 mg of 3-chloro-3-(3,4′-dichloro-5-methyl-biphenyl-4-yl)-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]decane-2,4-dione (title compound P1.9) as a gum.

المصدر