反応 #362825

反応方程式

potassium iodide

sodium nitrite

hydrochloric acid

3-methylthioaniline

→

3-iodo-1-methylthiobenzene

溶媒

water

water

water

反応条件

後処理

1. 1
   温度The mixture is warmed
2. 2
   workup.DISSOLUTIONdissolution
3. 3
   workup.ADDITIONare subsequently added slowly
4. 4
   温度while maintaining the temperature between 5 and 8° C
5. 5
   その他20 min
6. 6
   workup.ADDITIONare added over a period of 10 min
7. 7
   workup.STIRRINGthe mixture is then stirred at room temperature for 15 h
8. 8
   その他The oil which forms is separated from the aqueous phase by decantation
9. 9
   workup.ADDITIONan aqueous solution of sodium thiosulphate is then added to it
10. 10
    その他The aqueous phase is decanted
11. 11
    抽出the product is extracted with 100 ml of dichloromethane
12. 12
    洗浄The organic phase is washed with 100 ml of water
13. 13
    その他separated off
14. 14
    洗浄The organic phase is washed with 2 times 100 ml of water
15. 15
    その他separated off
16. 16
    乾燥dried over magnesium sulphate
17. 17
    ろ過filtered
18. 18
    濃縮concentrated to dryness under reduced pressure (50 kPa) at 40° C
19. 19
    その他The resulting product is purified by flash chromatography (eluent, cyclohexane) in order

実験手順

20 ml of distilled water and 20 ml of 12 N hydrochloric acid are placed, with stirring, in a three-necked flask, and 10 ml of 3-methylthioaniline are then added using a dropping funnel. The mixture is warmed to ensure dissolution and is then cooled down to 5° C. 5.86 g of sodium nitrite dissolved in 15 ml of water are subsequently added slowly, using a dropping funnel, while maintaining the temperature between 5 and 8° C. 20 min after having completed the addition, 13.57 g of potassium iodide dissolved in 15 ml of water are added over a period of 10 min and the mixture is then stirred at room temperature for 15 h. The oil which forms is separated from the aqueous phase by decantation, and an aqueous solution of sodium thiosulphate is then added to it. The aqueous phase is decanted and the product is extracted with 100 ml of dichloromethane. The organic phase is washed with 100 ml of water, and the aqueous phase is adjusted to pH 9 with concentrated sodium hydroxide solution, and then separated off. The organic phase is washed with 2 times 100 ml of water, separated off, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (50 kPa) at 40° C. The resulting product is purified by flash chromatography (eluent, cyclohexane) in order to yield 13 g of 3-iodo-1-methylthiobenzene in the form of a yellow liquid (Merck Silica 5719, Rf=0.8/cyclohexane).

出典