反応 #1275167

反応方程式

potassium iodide

sodium sulfite

sodium nitrite

3-(4-amino-3-difluoromethoxyphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

hydrochloric acid

urea

→

aimed product

収率 47.9%

5-(3,5-dichlorophenyl)-3-(3-difluoromethoxy-4-iodophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

収率 47.9%

溶媒

water

water

water

water

acetonitrile

反応条件

後処理

1. 1
   温度under cooling with ice
2. 2
   workup.ADDITIONAfter the completion of the addition dropwise
3. 3
   workup.STIRRINGto stir at the same temperature further for 20 minutes
4. 4
   workup.ADDITIONAfter the completion of the addition dropwise
5. 5
   workup.STIRRINGto stir at room temperature further for 30 minutes
6. 6
   workup.ADDITIONwas added in the reaction mixture
7. 7
   workup.STIRRINGstirred at room temperature for 30 minutes
8. 8
   抽出extracted with ethyl acetate (20 mL×2)
9. 9
   洗浄The combined organic phases were washed with water
10. 10
    乾燥dried over saturated sodium chloride aqueous solution
11. 11
    workup.DISTILLATIONanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
12. 12
    その他The residue was purified with silica gel column chromatography that

実験手順

In a solution of 1.00 g of 3-(4-amino-3-difluoromethoxyphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in a mixed solution of 10 mL of acetonitrile and 10 mL of water, 5 mL of concentrated hydrochloric acid was added, and a solution of 0.20 g of sodium nitrite in 2 mL of water was added dropwise slowly under cooling with ice and with stirring. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 20 minutes. Then, a solution of 0.47 g of potassium iodide in 1 mL of water was added dropwise carefully. After the completion of the addition dropwise, it was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, 0.041 g of urea was added in the reaction mixture, stirred at room temperature for 30 minutes, then a solution of 0.10 g of sodium sulfite in 5 mL of water was added, and extracted with ethyl acetate (20 mL×2). The combined organic phases were washed with water, and then dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (1:9) to obtain 0.60 g of the aimed product as yellow resinous substance.

出典